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Technická 5
166 28 Prague 6 – Dejvice
IČO: 60461373 / VAT: CZ60461373

Czech Post certified digital mail code: sp4j9ch

Copyright: UCT Prague 2015
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New PhD topics of our department: here

 All publications of our authors (since 2015): here

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k Phonebook of the Department    
     

Professors:

   
     

Prof. Radek Cibulka

e +420 22044 4182

d A 278c

b Radek.Cibulka@vscht.cz 

Head of Department www ResearcherID
     

Prof. Pavel Lhoták

e +420 22044 5055

d A 249

b Pavel.Lhotak@vscht.cz

  www  
     

Prof. Jaroslav Kvíčala

e +420 22044 4240

d A 278d

b Jaroslav.Kvicala@vscht.cz

  www  
     

Prof. Jiří Svoboda

e +420 22044 3688

d A 278e

b Jiri.Svoboda@vscht.cz

  www  
     

Associate Professors:

   
     

Assoc. Prof. Jan Budka

e +420 22044 4284

d A 251

b Jan.Budka@vscht.cz

DOC web editor www  
     

Assoc. Prof. Jana Hodačová

e +420 22044 4173

d A 270

b Jana.Hodacova@vscht.cz

  www  
     

Assoc. Prof. Michal Kohout

e +420 22044 5012

d A 258

b Michal.Kohout@vscht.cz

  www  
     

Assoc. Prof. Igor Linhart

e +420 22044 4165

d A 266

b Igor.Linhart@vscht.cz

  www  
     

Assoc. Prof. Tomáš Tobrman

e +420 22044 4245

d A 271

b Tomas.Tobrman@vscht.cz

 RIT www  
     

Assistant Professors:

   

Dr. Michal Himl

e +420 22044 4165

d A 266

b Michal.Himl@vscht.cz

  www  
     

Dr. Roman Holakovský

e +420 22044 4279

d A 255

b Roman.Holakovsky@vscht.cz

  www  
     

Dr. Petr Kovaříček

e +420 22044 2040

d B3 207

b Petr.Kovaricek@vscht.cz

www

Dr. Václav Kozmík

e +420 22044 4118

d A 308

b Vaclav.Kozmik@vscht.cz

  www  
     

Dr. Martin Krupička

e +420 220 444 173
d A 268
b Martin.Krupicka@vscht.cz

  www  
     

Dr. Ondřej Kundrát

e +420 22044 4280

d A 253

b Ondrej.Kundrat@vscht.cz

www ResearcherID 
     

Dr. Petra Ménová

e +420 22044 3686

d A 268

b Petra.Menova@vscht.cz

  www  

Dr. Pavla Perlíková

e +420 22044 2039

d B3 206

b Pavla.Perlikova@vscht.cz

www
     

Dr. Markéta Rybáčková

e +420 22044 4242

d A 259

b Marketa.Rybackova@vscht.cz

Secretary of Department

www  
     

Dr. Eva Svobodová

e +420 22044 4249

d A 260

b Eva.Svobodova@vscht.cz

  www  
     

Technicians:

   

Květa Bártová

e +420 22044 3686

d A 268

b Kveta.Bartova@vscht.cz

   
     

Ivana Bocková, MSc.

e +420 22044 4280

d A 250

b Ivana.Bockova@vscht.cz

   
     
Michaela Kadlecová 

e +420 22044 4276

d A 262

b Michaela.Kadlecova@vscht.cz
   
     

Martina Kovandová

e +420 22044 4279

d A 255

b Martina.Kovandova@vscht.cz

   
     

Vladimír Kuneš

e +420 22044 4277

d A L06

b Vladimir.Kunes@vscht.cz

   
     

Jana Netušilová

e +420 22044 4164

d A 278a

b Jana.Netusilova@vscht.cz

Administrative Support of Department  
     

Markéta Slabochová, MSc.

e +420 22044 4059 

d A 308  

b Marketa.Slabochova@vscht.cz

Economist of Department  
     

Helena Štenglová 

e +420 22044 4278 

d A 257 

b Helena.Stenglova@vscht.cz

   
     

Ing. David Tetour

e +420 22044 4173

d A270

b David.Tetour@vscht.cz

Marta Tokárová 

e +420 220 444 245 

d A 271 

b Marta.Tokarova@vscht.cz

   
     

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Essential Information for Current Students



Bachelor Students

Master Students

PhD Students

Lectures delivered by members of the Department

  • Toxicology and ecology
  • Organic chemistry I, II and III
  • Structural analysis
  • Reactivity of organic compounds
  • Molecular design
  • Organic synthesis I and II
  • Quantum organic chemistry
  • Farmacochemistry
  • Organic stereochemistry
  • Organometallic chemistry
  • Organic chemistry of selected elements

Repository of the theses

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Prof. Andrea Brancale,  Dr. Petra Cuřínová

      Our research focus is on the design, synthesis, and development of novel biologically active molecules, in particular, but not exclusively, of anticancer and antiviral compounds. Our main objective is to contribute towards the discovery and the development of new therapies against diseases with a clear unmet medical need. To achieve this, we combine a variety of drug design and approaches, from classical medicinal chemistry to more advanced computer-based drug design methods. The highly interdisciplinary and collaborative nature of our research is reflected in our publications, and through the extensive network of collaboration we have established during the years.

 ◳ IMG_5966(1) (jpg) → (šířka 450px)

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Staff:

 ◳ andrea (jpg) → (ořez 215*215px)


Prof. Andrea Brancale



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phone:

 +420 220 442 931


e-mail:

Andrea.Brancale@vscht.cz

 ◳ petra (jpg) → (originál)


Dr. Petra Cuřínová



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phone:

 +420 220 442 930


e-mail:

Petra.Curinova@vscht.cz 

Technician:

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Zdeňka Hrbáčková



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e-mail:

Zdenka.Hrbackova@vscht.cz


Permanent students:

3rd year:

 

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Jana Ferenczeiová


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Jan Drahorád


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Kristián Schwan


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Lenka Vondráčková


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Anna Velebová


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2nd year:

 

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Jakub Janáč


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Lívia Platková


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Visiting students and reserchers:

2022

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Chiara Siguri, MSc


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University of Cagliari
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Alessia Onali. MSc


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University of Cagliari
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Sarah Van Den Bussche


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University of Poitiers
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Camille Devilliers


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University of Poitiers

2023

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Marianna Bufano, PhD


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University of Rome
„La Sapienza“
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Gregory Mathez, MSc


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Centre Hospitalier Universitaire Vaudois, Lausanne
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Milena Nicolosi, MSc


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University of Catania
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Michelle Femi Agbetuyi


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Université Bourgogne

Franche-Comté

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Archie McCulloch


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high school student

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Research projects:

RNA-binding agents as antiviral compounds

In this project we aim to design and synthesise a series of new small molecules with drug-like properties, that are able to selectively bind to viral RNA, blocking viral replication.

Protein degraders as antivirals

The main goal of this project is to prepare novel PROTACs compounds that are able to promote the degradation of viral proteins by the natural cellular mechanisms.

Modulators of mitochondria dynamics

Mitochondrial disfunctions are responsible for different diseases. In our group we are working on compounds that affect mitochondria dynamics. These molecules are potentially useful against cancer and other therapeutic areas.

Novel antiviral compounds against Flaviviridae

This project is focused on the optimization of the previously identified hit compounds showing activity against Flaviviruses (e.g., Dengue, Zika).

From natural compounds to small, drug-like molecules

Natural compounds are a good source of bioactive compounds. However, they are often not developed as drugs. In this project we are designing drug-like analogues of a natural compound with neuroprotective activity.

 

 

 

 

 

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 ◳ News_17 (jpg) → (originál)


Prof. Radek Cibulka, Ph.D.

 ◳ IMG_1681 (png) → (originál)

Chemistry_Europe_Fellows Class 2020/21


 ◳ News_15 (jpg) → (originál)


Adam Pokluda - IGRA

As a co-researcher, Adam Pokluda from our laboratory will participate on the prestigious IGRA grant at the University of Chemistry and Technology, Prague entitled "Alloxazine photon catching antenna for molecular switches in organic electronics". The main researcher is Marek Čubiňák from the Institute of Organic Chemistry. The Institute of Physical Chemistry also participates in the project.


Paper in a prestigious journal:

Graml A., Neveselý T., Kutta R.-J., Cibulka R., König B.: Deazaflavin reductive photocatalysis involves excited semiquinone radicals Nature Comm. 2020, 11, 3174.  DOI: 10.1038/s41467-020-16909-y. https://rdcu.be/b47PV


News and views paper in Nature:

Cibulka R.: Strong chemical reducing agents produced by light Nature 580, 31-32 (2020). DOI:10.1038/d41586-020-00872-1. https://www.nature.com/articles/d41586-020-00872-1


Highly cited papers

Article (Org. Lett. 2019, 21, 114-119) published by our group in cooperation with the group of prof. Roithová met the criteria of web of science for "Highly cited papers“ (As of November/December 2019, this paper received enough citations to place it in the top 1% of the academic field of Chemistry based on a highly cited threshold for the field and publication year).

Abstract: 

obr. 2020 (originál)

We report a system with ethylene-bridged flavinium salt 2b which catalyzes the aerobic oxidation of toluenes and benzyl alcohols with high oxidation potential (Eox > +2.5 V vs SCE) to give the corresponding benzoic acids under visible light irradiation. This is caused by the high oxidizing power of excited 2b (E(2b*) = +2.67 V vs SCE) involved in photooxidation and by the accompanying dark organocatalytic oxygenation provided by the in situ formed flavin hydroperoxide 2b-OOH

DOI:10.1021/acs.orglett.8b03547. 


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Prof. Radek Cibulka
building A, room 278c
k + 420 220 44 4182
b Radek.Cibulka@vscht.cz
 
Dr. Roman Holakovský
building A, room 255
k + 420 220 44 4279
b Roman.Holakovsky@vscht.cz
 

Dr. Eva Svobodová

building A, room 260
k + 420 220 44 4249
      + 420 220 44 4279
b Eva.Svobodova@vscht.cz
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Employees:

  • Prof. Radek Cibulka      (CV)
  • Dr. Eva Svobodová (CV)
  • Dr. Roman Holakovský (CV)
  • Dr. Tetiana Pavlovska (post-doc)
  • Martina Kovandová

 

Ph.D. students:

  • Ing. Róbert Obertík
  • Ing. Adam Pokluda
  • Amal Hassan Tolba, MSc.
  • Ing. Ivana Weisheitelová

 

Students:

  • Petra Míková
  • Ekaterina Zubova
  • František Vávra
  • Jan Svoboda
  • Rostislav Sponar
  • David Král Lesný
  • Jan Řeháček
  • Zuzana Abdelfattah
  • Marie Rozmušová

 

Students Collaborations:

  • Ing. Jakub Copko
  • Ing. Jan Zelenka (UK)
  • Ing. Václav Chmela
  • Barbora-Eva Eliášová

 

Collaborations:

  • Prof. Marek Sikorski 
  • Prof. Jiří Ludvík 
  • Prof. Burkhard König
  • Dr. Ullrich Jahn
  • Dr. Tomáš Slanina

 

Guests:

  • Ester Sans Panades (Spain, 2021)
  • Vincent George (Germany, 2019)
  • Dharmik Gadhiya (Polsko, 2019)
  • Killiann Heinz (Francie, 2019, 2020)
  • Tribout Camille (Francie, 2018)
  • Thibaud Bailly (France, 2018)
  • Jehanne Grimmer (France, 2017)
  • Sarah Bailly (France, 2017)
  • Guillaume Hoffmann (France, 2016)
  • Dr. Dorota Prukala (Poland, 2014, 2015)
  • Nadia Ryter (Switzerland, 2010)
  • Smita Gunnoo (UK, 2008)
  • Andreja Čondor (Croatia, 2007)
  • Serkan Sayin (Turkey, 2007)
  • Jenna Scotcher (UK, 2006)
  • Baptiste Plancq (France, 2005)
  • Markus W. Kriegl (Austria, 2005)
  • Tilman Schulz (Germany, 2004)
  • Yuliya Milaslavina (Belarus, 2002)
  • Rina Matsumi (Japan, 2001)

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Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling

DOI:10.1021/acs.joc.2c02168

Abstract:
 ◳ jorgchem2022 (png) → (originál)Palladium-catalyzed Suzuki reactions of brominated flavin derivatives (5-deazaflavins, alloxazines, and isoalloxazines) with boronic acids or boronic acid esters that occur readily under mild conditions were shown to be an effective tool for the synthesis of a broad range of 7/8-arylflavins. In general, the introduction of an aryl/heteroaryl group by means of a direct C–C bond has been shown to be a promising approach to tuning the photophysical properties of flavin derivatives. The aryl substituents caused a bathochromic shift in the absorption spectra of up to 52 nm and prolonged the fluorescence lifetime by up to 1 order of magnitude. Moreover, arylation of flavin derivatives decreased their ability to generate singlet oxygen.

Highly Chemoselective Catalytic Photooxidations by Using Solvent as a Sacrificial Electron Acceptor

DOI:10.1002/chem.202202487

Abstract:
Catalyst recovery is an integral part of photoredox catalysis. It is often solved by adding another component-a sacrificial agent-whose role is to convert the catalyst back into its original oxidation state. However, an additive may cause a side reaction thus decreasing the selectivity and overall efficiency. Herein, we present a novel approach towards chemoselective photooxidation reactions based on suitable solvent-acetonitrile acting simultaneously as an electron acceptor for catalyst recovery, and on anaerobic conditions. This is allowed by the unique properties of the catalyst, 7,8-dimethoxy-3-methyl-5-phenyl-5-deazaflavinium chloride existing in both strongly oxidizing and reducing forms, whose strength is increased by excitation with visible light. Usefulness of this system is demonstrated in chemoselective dehydrogenations of 4-methoxy- and 4-chlorobenzyl alcohols to aldehydes without over-oxidation to benzoic acids achieving yields up to 70 %. 4-Substituted 1-phenylethanols were oxidized to ketones with yields 80–100 % and, moreover, with yields 31-98 % in the presence of benzylic methyl group, diphenylmethane or thioanisole which are readily oxidized in the presence of oxygen but these were untouched with our system. Mechanistic studies based on UV-Vis spectro-electrochemistry, EPR and time-resolved spectroscopy measurements showed that the process involving an electron release from an excited deazaflavin radical to acetonitrile under formation of solvated electron is crucial for the catalyst recovery.

 ◳ chem202202487-toc-0001-m (png) → (originál)

New way to drive photoredox catalysis: Highly chemoselective photooxidations of benzylic alcohols to carbonyl compounds in the presence of various easily-oxidizable groups are possible in a simple oxygen-free system consisting of a substrate, unique deazaflavinium catalyst and acetonitrile which acts simultaneously as a sacrificial electron acceptor and solvent.

Tuning Deazaflavins Towards Highly Potent Reducing Photocatalysts Guided by Mechanistic Understanding – Enhancement of the Key Step by the Internal Heavy Atom Effect

DOI:10.1002/chem.202200768

Abstract:
Deazaflavins are well suited for reductive chemistry acting via a consecutive photo-induced electron transfer, in which their triplet state and semiquinone – the latter is formed from the former after electron transfer from a sacrificial electron donor – are key intermediates. Guided by mechanistic investigations aiming to increase intersystem crossing by the internal heavy atom effect and optimising the concentration conditions to avoid unproductive excited singlet reactions, we synthesised 5-aryldeazaflavins with Br or Cl substituents on different structural positions via a three-component reaction. Bromination of the deazaisoalloxazine core leads to almost 100 % triplet yield but causes photo-instability and enhances unproductive side reactions. Bromine on the 5-phenyl group in ortho position does not affect the photostability, increases the triplet yield, and allows its efficient usage in the photocatalytic dehalogenation of bromo- and chloroarenes with electron-donating methoxy and alkyl groups even under aerobic conditions. Reductive powers comparable to lithium are achieved.

 ◳ chemeurj2022_1 (png) → (originál) Inspired by nature and based on mechanistic understanding, we designed deazaflavins (dFl) with reducing powers comparable to Li which function via the consecutive photo-induced electron transfer (conPET) mechanism independently on molecular oxygen. The internal heavy atom effect (IHAE) by introducing bromine into the photocatalyst enhances considerably the key triplet pathway via a triplet-born radical pair. Furthermore, an optimal concentration of the sacrificial electron donor (Ssac) is required for bypassing the unproductive reaction via the singlet-born radical pair.

 

Photophysical properties of alloxazine derivatives with extended aromaticity – Potential redox-sensitive fluorescent probe

DOI: 10.1016/j.saa.2022.120985

Abstract:
 ◳ Spectrocha (png) → (originál)The spectral and photophysical properties of two four-ring alloxazine derivatives, naphtho[2,3-g]pteridine-2,4(1H,3H)-dione (1a) and 1,3-dimethylnaphtho[2,3-g]pteridine-2,4(1H,3H)-dione, (1b) were studied. The propensity of 1a for excited-state proton transfer reactions in the presence of acetic acid as a catalyst was also studied, showing no signature of the reaction occurring. In addition, quenching of 1a fluorescence by acetic acid was investigated. Singlet and triplet states and spectral data for 1a and 1b were calculated using density functional theory TD-DFT at B3LYP/6-31G(d) and UB3LYP levels. Finally, fluorescence lifetime imaging microscopy (FLIM) using 1a and 1b as fluorescence probes was applied to in vitro human red blood cells (RBCs) with and without tert-butyl hydroperoxide (TB) as an oxidising agent. To evaluate and compare the effects of 1a and 1b on the redox properties of RBCs, the fluorescence lifetime, amplitude and fractional intensities were calculated, and phasor plot analysis was performed. The results obtained show the appearance of a new proximal cluster in the phasor fingerprint of RBCs in the presence of 1b and a shorter fluorescence lifetime of RBCs in the presence of 1a.

Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

doi.org/10.1021/acs.orglett.1c02391

 ◳ ol1c02391_0005 (gif) → (originál)Abstract:
We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.

Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films

 doi.org/10.1002/cplu.202100092

 ◳ cplu202100092-toc-0001-m (png) → (originál)The complex characterization of a flavo[7]helicene conjugate is reported in this work. This conjugate combines inherent helical chirality with redox activity, which was studied in solution (both aqueous and organic phases), in layers (electropolymers), and in the solid state (a single crystal).

Abstract:
This work reports on the preparation and structural characterization of flavo[7]helicene 1 (flavin-[7]helicene conjugate), which was subsequently characterized at the molecular level in either an aqueous environment or an organic phase, at the supramolecular level in the form of polymeric layers, and also embedded in a lipidic mesophase environment to study the resulting properties of such a hybrid relative to its parent molecules. The flavin benzo[g]pteridin-2,4-dione (isoalloxazine) was selected for conjugation because of its photoactivity and reversible redox behavior. Compound 1 was prepared from 2-nitroso[6]helicene and 6-methylamino-3-methyluracil, and characterized using common structural and spectroscopic tools: circular dichroism (CD), circularly polarized luminescence (CPL) spectroscopy, cyclic voltammetry (CV), and DFT quantum calculations. In addition, a methodology that allows the loading of 1 enantiomers into an internally nanostructured lipid (1-monoolein) matrix was developed.

Robust Photocatalytic Method Using Ethylene-Bridged Flavinium Salts for the Aerobic Oxidation of Unactivated Benzylic Substrates

 doi.org/10.1002/adsc.202100024

 ◳ adsc202100024-toc-0001-m (png) → (originál)Abstract:
7,8-Dimethoxy-3-methyl-1,10-ethylenealloxazinium chloride (1a) was found to be a superior photooxidation catalyst among substituted ethylene-bridged flavinium salts (R=7,8-diMeO, 7,8-OCH2O-, 7,8-diMe, H, 7,8-diCl, 7-CF3 and 8-CF3). Selection was carried out based on structure vs catalytic activity and properties relationship investigations. Flavinium salt 1a proved to be robust enough for practical applications in benzylic oxidations/oxygenations, which was demonstrated using a series of substrates with high oxidation potential, i. e., 1-phenylethanol, ethylbenzene, diphenylmethane and diphenylmethanol derivatives substituted with electron-withdrawing groups (Cl or CF3). The unique capabilities of 1a can be attributed to its high photostability and participation via a relatively long-lived singlet excited state, which was confirmed using spectroscopic studies, electrochemical measurements and TD-DFT calculations. This allows the maximum use of the oxidation power of 1a, which is given by its singlet excited state reduction potential of +2.4 V. 7,8-Dichloro-3-methyl-1,10-ethylenealloxazinium chloride (1 h) can be used as an alternative photocatalyst for even more difficult substrates.

Photocatalytic Oxidative [2+2] Cycloelimination Reactions with Flavinium Salts: Mechanistic Study and Influence of the Catalyst Structure

doi.org/10.1002/cplu.202000767

 ◳ cplu202000767-toc-0001-m (jpg) → (originál)

Making light work: Alloxazinium salts (flavin derivatives) are very strong oxidizing agents in their excited singlet and triplet states after absorption of visible light. When suitably substituted, these salts are relatively photostable and robust for practical applications in photoredox catalysis, as shown by the detailed mechanistic study on the [2+2] photocycloelimination reaction mediated by 7,8-dimethoxy-1,3-dimethylalloxazinium perchlorate.

Abstract:
Flavinium salts are frequently used in organocatalysis but their application in photoredox catalysis has not been systematically investigated to date. We synthesized a series of 5-ethyl-1,3-dimethylalloxazinium salts with different substituents in the positions 7 and 8 and investigated their application in light-dependent oxidative cycloelimination of cyclobutanes. Detailed mechanistic investigations with a coumarin dimer as a model substrate reveal that the reaction preferentially occurs via the triplet-born radical pair after electron transfer from the substrate to the triplet state of an alloxazinium salt. The very photostable 7,8-dimethoxy derivative is a superior catalyst with a sufficiently high oxidation power (E*=2.26 V) allowing the conversion of various cyclobutanes (with Eox up to 2.05 V) in high yields. Even compounds such as all-trans dimethyl 3,4-bis(4-methoxyphenyl)cyclobutane-1,2-dicarboxylate can be converted, whose opening requires a high activation energy due to a missing pre-activation caused by bulky adjacent substituents in cis-position.

The crystal structure of 2-(4-((carbamimidoylthio)methyl)-benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2

doi.org/10.1515/ncrs-2021-0417

 ◳ graphic_j_ncrs-2021-0417_fig_001 (jpg) → (originál)

Crystal structure of 2-(3-((carbamimidoylthio)methyl)-benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2

 doi.org/10.1515/ncrs-2021-0418

 ◳ graphic_j_ncrs-2021-0418_fig_001 (jpg) → (originál)

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2024

Weisheitelová I., Varma N., Chudoba J., Burdziński G., Sikorski M., Cibulka R.: Catalyst-free aerobic photooxidation of sensitive benzylic alcohols with chemoselectivity controlled by DMSO solvent. Green Chem. 2024 accepted. DOI:10.1039/D4GC00087K

Burešová Z., Gobeze H. B., Grygarová M., Pytela O., Klikar M., Obertík R., Cibulka R., Islam T., Schanze K. S., Bureš F.: Dicyanopyrazine Photoredox Catalysts: Correlation of Efficiency with Photophysics and Electronic Structure. Journal of Catalysis 2024, 430, 115348.  DOI:10.1016/j.jcat.2024.115348

Zubová E., Pokluda A. Dvořáková H., Krupička M., Cibulka R.: Exploring the Reactivity of Flavins with Nucleophiles Using a Theoretical and Experimental Approach. ChemPlusChem 2024, e202300547. DOI:10.1002/cplu.202300547.

2023

Pavlovska T., Weisheitelová I., Pramthaisong C., Sikorski M., Jahn U., Cibulka R.: Primary and Secondary Amines by Flavin‐Photocatalyzed Consecutive Desulfonylation and Dealkylation of Sulfonamides. Adv. Synth. Catal. 20233654662. DOI:10.1002/adsc.202300843.

Golczak A., Prukała D., Gierszewski M., Cherkas V., Kwiatek D., Kubiak A., Varma N., Pedziński T., Murphree S., Cibulka R., Mrówczińska L., Kolanovski J. L., Sikorski M.: Tetramethylalloxazines as efficient singlet oxygen photosensitizers and potential redox‑sensitive agents. Scientific Reports 2023, 13, 13426. DOI:10.1038/s41598-023-40536-4

Insińska-Rak M., Golczak A., Gierszewski M., Anwar Z., Cherkas V., Kwiatek D., Sikorska E., Khmelinskii I., Burdziński G., Cibulka R., Mrówczyńskag L., Kolanowskic J. L. and Sikorski M.: 5-Deazaalloxazine as photosensitizer of singlet oxygen and potential redox-sensitive agent. Photochem. Photobiol. Sci. 2023. DOI:10.1007/s43630-023-00401-9  

Pokluda A., Zubova E., Chudoba J., Krupička M., Cibulka R.: Catalytic Artificial Nitroalkane Oxidase – a Way Towards Organocatalytic Umpolung. Org. Biomol. Chem. 2023, 21, 2768 - 2774.  DOI:10.1039/d3ob00101f.

2022

Čubiňák M., Varma N., Oeser P., Pokluda A., Pavlovska T., Cibulka R., Sikorski M., Tobrman T. Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling. J. Org. Chem. 2022. DOI:10.1021/acs.joc.2c02168

Obertík R., Chudoba J., Šturala J., Tarábek J., Ludvíková L., Slanina T., König B., Cibulka R.: Chem. Eur. J. 2022, accepted as VIP. DOI:10.1002/chem.202202487.

Pavlovska T., Král Lesný D., Svobodová E., Hoskovcová I., Archipowa N., Kutta R. J., Cibulka R. Tuning Deazaflavins Towards Highly Potent Reducing Photocatalysts Guided by Mechanistic Understanding - Enhancement of the Key Step by the Internal Heavy Atom Effect. Chem. Eur. J. 2022, 28, e20220076. Hot Paper. DOI:10.1002/chem.202200768.

Golczak A., Insińska-Rak M., Davoudpour A., Saeed D. H., Ménová P., Mojr V., Cibulka R., Khmelinskii V., Mrówczyńska L., Sikorski M. Photophysical properties of alloxazine derivatives with extended aromaticity – potential redox sensitive fluorescent probe. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, volume 272, 120985, 2022. DOI: 10.1016/j.saa.2022.120985.

2021

Tolba A. H., Krupička M., Chudoba J., Cibulka R.: Amide bond formation via aerobic photooxidative coupling of alde-hydes with amines catalyzed by a riboflavin derivative Org. Lett. 2021, 23, 17, 6825–6830. DOI:10.1021/acs.orglett.1c02391.

Radek Cibulka (a prof. M. Fraaije z Univerzity v Groningenu) editory knihy „Flavin-Based catalysis“ v nakladatelství Wiley-VCH. Zároveň členové naší skupiny připravili tři z dvanácti kapitol v této knize:
Pavlovska, T.; Cibulka, R., Structure and Properties of Flavins. pp 1-27.
Cibulka, R.; Fraaije, M. W., Modes of Flavin-Based Catalysis. pp 97-124.
Svobodová, E.; Cibulka, R., New Applications of Flavin Photocatalysis. pp 265-291.
Wiley-VCH - Flavin-Based Catalysis

Jakubec M., Novák D., Zatloukalová M., Sýkora J., Císařová I., Cibulka R., Favereau L., Crassous J., Bilewicz R., Hrbáč J., Storch J., Žádný J., Vacek J.: Flavin-Helicene Amphiphilic Hybrids: Synthesis, Characterization, and Preparation of Surface-Supported Films  ChemPlusChem 202186, 982-990. DOI: 10.1002/cplu.202100092.

Pokluda A., Anwar Z., Boguschová V., Anusiewicz I., Skurski P., Sikorski M., Cibulka R.: Robust photocatalytic method using ethylene-bridged flavinium salts for the aerobic oxidation of unactivated benzylic substrates Adv. Synth. Catal. 2021 363, 4371-4379. VIP, DOI: 10.1002/adsc.202100024.

 Cover Feature“

Hartman T., Reisnerová M., Chudoba J., Svobodová E., Archipowa N., Kutta R. J., Cibulka R.: Photocatalytic Oxidative [2+2] Cycloelimination Reactions with Flavinium Salts: Mechanistic Study and Influence of the Catalyst Structure ChemPlusChem 2021, 86, 373–386. DOI: 10.1002/cplu.202000767.

Cover Feature“

Eigner, Václav and Holakovský, Roman. "The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2Zeitschrift für Kristallographie - New Crystal Structures, vol. , no. , 2021.  doi.org/10.1515/ncrs-2021-0417

Eigner, Václav and Holakovský, Roman. "Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2 " Zeitschrift für Kristallographie - New Crystal Structures, vol. , no. , 2021.  doi.org/10.1515/ncrs-2021-0418

2020

Graml A., Neveselý T., Kutta R.-J., Cibulka R., König B.: Deazaflavin reductive photocatalysis involves excited semiquinone radicals Nature Comm. 2020, 11, 3174.  DOI: 10.1038/s41467-020-16909-y. https://rdcu.be/b47PV

Cibulka R.: Strong chemical reducing agents produced by light Nature 580, 31-32 (2020). DOI: 10.1038/d41586-020-00872-1. https://www.nature.com/articles/d41586-020-00872-1

Tolba A. H., Vávra F., Chudoba J., Cibulka R: Tuning flavin-based photocatalytic systems for application in the mild chemoselective aerobic oxidation of benzylic substrates Eur. J. Org. Chem. 2020, 1579–1585. DOI:10.1002/ejoc.201901628Special issue Photochemical synthesis.

Schlosser J., Cibulka R., Groß P., Ihmels H., Mohrschladt C. J.: Visible-light induced di-π-methane rearrangement of dibenzobarrelene derivatives ChemPhotoChem 2020, 4, 132. DOI:10.1002/cptc.201900221.

2019

Zelenka, J.; Cibulka, R., Roithová, J.: Flavinium catalyzed photooxidation: Detection and characterization of elusive peroxyflavinium intermediates. Angew. Chem. Int. Ed. 2019, 58, 15412-15420. DOI:10.1002/anie.201906293. VIP 

cover picture (šířka 215px)

März M., Babor M., Cibulka R.: Flavin Catalysis Employing an N(5)-Adduct: An Application in the Aerobic Organocatalytic Mitsunobu Reaction Eur. J. Org. Chem. 2019, 20, 3264-3268. DOI:10.1002/ejoc.201900397.

Pokluda A., Kohout M., Chudoba J., Krupička M., Cibulka R.: Nitrosobenzene – Reagent for the Mitsunobu Esterification Reaction ACS Omega 2019, 4, 5012-5018. DOI:10.1021/acsomega.8b03551.

Valenta L., Kovaříček P., Valeš V., Bastl Z., Drogowska K. A., Verhagen T. A., Cibulka R., Kalbáč M.: Spatially resolved covalent functionalization patterns on graphene Angew. Chem. Int. Ed. 2019, 58, 1324-1328. DOI:10.1002/anie.201810119.
https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201810119

Zelenka J., Svobodová E., Tarábek J., Hoskovcová I., Boguschová V., Bailly S., Sikorski M., Roithová J., Cibulka R.: Combining flavin photocatalysis and organocatalysis: metal-free aerobic oxidation of unactivated benzylic substrates Org. Lett. 2019, 21, 114-119. DOI:10.1021/acs.orglett.8b03547.  Highly cited paper (WOS).

2018

März M., Kohout M., Neveselý T., Chudoba J., Prukala D., Niziński S., Sikorski M., Burdziński G., Cibulka R.: Azodicarboxylate-free esterification with triphenylphosphine mediated by flavin and visible light: method development and stereoselectivity control Org. Biomol. Chem. 2018, 16, 6809-6817. DOI: 10.1039/C8OB01822G.

Holakovský R., Cibulka R., Konečková E., März M.: Způsob stanovení enantiomerní čistoty chirálních sulfoxidů pomocí 1H NMR analýzy, PV 2016-92, č. 307419. Pozn. 2018

König B., Kümmel S., Svobodová E.  and Cibulka R.: Flavin photocatalysis, in Physical Sciences Reviews, 3 (8), 20170168, ISSN (Online) 2365-659X. DOI: 10.1515/psr-2017-0168.

Slavíček P., Cibulka R.: A chemici nebudou mít co žrát… (Strojové učení v chemii) Vesmír 97, 2018 (5), 300-301.
https://vesmir.cz/cz/casopis/archiv-casopisu/2018/cislo-5/a-chemici-nebudou-mit-co-zrat.html

Muchová E., Bezek M., Suchan J., Cibulka R., Slavíček P.: Molecular Dynamics and Metadynamics Simulations of [2+2] Photocycloaddition Int. J. Quantum Chem. 2018, 118, e25534. DOI:10.1002/qua.25534

Cuřínová P., Dračínský M., Jakubec M, Tlustý M., Janků K., Izák P., Holakovský R.: Enantioselective complexation of 1phenylethanol with chiral compounds bearing urea moiety. Chirality 2018, 30, 798806. DOI:10.1002/chir.22855.

Mojr V., Pitrová G., Straková K., Prukala D., Brazevic S., Svobodová E., Hoskovcová I., Burdziński G., Slanina T., Sikorski M., Cibulka R.: Flavin Photocatalysts for  visible Light [2+2] Cycloadditions: Structure, Reactivity and Reaction Mechanism ChemCatChem 2018, 10, 849-858. DOI:10.1002/cctc.201701490.

Kurfiřt M., Špačková J., Svobodová E., Cibulka R.: Flavin derivatives immobilized on mesoporous silica: a versatile tool in visible-light photooxidation reactions Monatshefte Chem. 2018, 149, 863-869. DOI:10.1007/s00706-017-2127-1.

2017

Žurek J., Svobodová E., Šturala J., Dvořáková H., Svoboda J., Cibulka R.: Chiral ethylene-bridged flavinium salts: The stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties Tetrahedron Asymmetry 2017, 28, 1780-1791, DOI:10.1016/j.tetasy.2017.10.029

Sofer, Z., Luxa, J., Bouša, D., Sedmidubský, D., Lazar, P., Hartman, T., Hardtdegen, H. and Pumera, M.: The Covalent Functionalization of Layered Black Phosphorus by Nucleophilic Reagents. Angew. Chem. Int. Ed. 2017, 56, 9891–9896. DOI:10.1002/anie.201705722

März M., Kohout M., Chudoba J., Cibulka R.: Photocatalytic Esterification under Mitsunobu Reaction Conditions Mediated by Flavin and Visible Light Org. Biomol. Chem. 2017, 15, 1970-1975.  DOI:10.1039/C6OB02770A, highlighted in http://www.organic-chemistry.org/Highlights/2018/12March.shtm

Kolderová, N.; Neveselý, T.; Šturala, J.; Kuchař, M.; Holakovský, R.; Kohout, M.: Enantioseparation of Chiral Sulfoxides on Amylose-Based Columns: Comparison of Normal Phase Liquid Chromatography and Supercritical Fluid Chromatography. Chromatographia 2017, 80, 547-557. DOI: 10.1007/s10337-016-3234-6

Špačková J., Svobodová E., Hartman T., Stibor I., Kopecká J., Cibulková J., Chudoba J., Cibulka R.: Visible Light [2+2] Photocycloaddition Mediated by Flavin Derivative Immobilized on Mesoporous Silica, ChemCatChem 2017, 9, 1177-1181. DOI:10.1002/cctc.201601654

Jirásek M., Straková K., Neveselý T., Svobodová E., Rottnerová Z., Cibulka R.: Flavin-Mediated Visible Light [2+2] Photocycloadditon of Nitrogen and Sulfur-Containing Dienes, Eur. J. Org. Chem. 2017, 2139-2146. DOI:10.1002/ejoc.201601377

2016

Hartman T., Cibulka R.: Photocatalytic Systems with Flavinium Salts: From Photolyase Models to Synthetic Tool for Cyclobutane Ring Opening, Org. Lett. 2016, 18, 3710-3713. DOI:10.1021/acs.orglett.6b01743

Bím, D.; Svobodová, E.; Eigner, V.; Rulíšek, L.; Hodačová, J.: Copper(II) and Zinc(II) Complexes of Conformationally Constrained Polyazamacrocycles as Efficient Catalysts for RNA Model Substrate Cleavage in Aqueous Solution at Physiological pH, Chem. Eur. J. 2016, 22, 10426-10437.  DOI:10.1002/chem.201683062

Neveselý T., Svobodová E., Chudoba J., Sikorski M., Cibulka R.: Efficient metal-free aerobic photooxidation of sulfides to sulfoxides mediated by a vitamin B2 derivative and visible light, Adv. Synth. Catal. 2016, 358, 1654–1663. DOI:10.1002/adsc.201501123 VIP.

Holakovský R., Cibulka R., Konečková E., März M.: Močovina na bázi binaftalenu pro stanovení enantiomerní čistoty chirálních sulfoxidů pomocí 1H-NMR analýzy. Patent č. 305 940 (PV: 00710-14)

2015

García, Y. R.; Zelenka, J.; Pabon, Y. V.; Iyer, A.; Buděšínský, M.; Kraus, T.; Smith, C. I. E.; Madder, A.: Cyclodextrin–peptide conjugates for sequence specific DNA binding, Org. Biomol. Chem. 2015, 13, 5273–5278. DOI:10.1039/C5OB00609K

Bousa, D.; Jankovsky, O.; Sedmidubsky, D.; Luxa, J.; Sturala, J.; Pumera, M.; Sofer, Z.: Mesomeric Effects of Graphene Modified with Diazonium Salts: Substituent Type and Position Influence its Properties, Chem. Eur. J. 2015, 21, 17728-17738. DOI:10.1002/chem.201502127

Tomanová P., Šturala J., Buděšínský M., Cibulka R.: A click chemistry approach towards flavin-cyclodextrin conjugates – bioinspired sulfoxidation catalysts, Molecules 2015, 20, 19837-19848. DOI:10.3390/molecules201119667

Holakovský R., März M., Cibulka R.: Urea derivatives based on a 1,1'-binaphthalene skeleton as chiral solvating agents for sulfoxides, Tetrahedron: Asymmetry 2015, 26, 1328-1334. DOI:10.1016/j.tetasy.2015.10.011

Hartman J., Šturala J., Cibulka R.: Two-phase Oxidations with Aqueous Hydrogen Peroxide Catalysed by Amphiphilic Pyridinium and Diazinium Salts, Adv. Synth. Catal. 2015, 357, 3573-3586. DOI:10.1002/adsc.201500687

Mojr V., Svobodová E., Straková K., Neveselý T., Chudoba J., Dvořáková H., Cibulka R.: Tailoring Flavins for Visible Light Photocatalysis: Organocatalytic [2+2] Cycloadditions Mediated by a Flavin Derivative and Visible Light, Chem. Comm. 201551, 12036 – 12039. DOI:10.1039/C5CC01344E

Sofer, Z.; Jankovský, O.; Šimek, P.; Sedmidubský, D.; Šturala, J.; Kosina, J.; Mikšová, R.; Macková, A.; Mikulics, M.; Pumera, M.: Insight into the Mechanism of the Thermal Reduction of Graphite Oxide: Deuterium-Labeled Graphite Oxide Is the Key, ACS Nano; 2015, 9, 5478-5485. DOI:10.1021/acsnano.5b01463

Šturala J., Boháčová S., Chudoba J., Metelková R., Cibulka R.: Electron-deficient Heteroarenium salts – an Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations, J. Org. Chem., 2015, 80, 2676-2699. DOI:10.1021/jo502865f

Cibulka R.: Artificial flavin systems for chemoselective and stereoselective oxidations (Microreview), Eur. J. Org. Chem., 2015, 915-932. DOI:10.1002/ejoc.201403275 + Cover picture

2014

Zelenka J., Hartman T. Klímová K., Hampl F., Cibulka R.: Phase-transfer catalysis in oxidations based on the covalent bonding of hydrogen peroxide to amphiphilic flavinium salts, ChemCatChem, 2014, 6, 2843-2846. DOI:10.1002/cctc.201402533

Kotoučová H., Strnadová I., Kovandová M., Chudoba J., Dvořáková H., Cibulka R.: Biomimetic aerobic oxidative hydroxylation of arylboronic acids to phenols catalysed by a flavin derivative, Org. Biomol. Chem., 2014, 12, 2137-2142. DOI:10.1039/C3OB42081G

2013

Ménová P., Dvořáková H., Eigner V. Ludvík J., Cibulka R.: Electron-deficient alloxazinium salts: efficient organocatalysts of mild and chemoselective sulfoxidations with hydrogen peroxide, Adv. Synth. Catal., 2013, 355, 3451-3462. DOI:10.1002/adsc.201300617

Kümmel S., Cibulka R., König B.: “Flavin Photocatalysis” in Chemical Photocatalysis (Burkhard König, ed.), de Gruyter, Berlin 2013, ISBN: 978-3-11-026924-6.

Jurok R., Hodačová J., Eigner V., Dvořáková H., Setnička V., Cibulka R.: Planar chiral flavinium salts: Synthesis and evaluation of the effect of substituents on the catalytic efficiency in enantioselective sulfoxidation reactions, Eur. J. Org. Chem., 2013, 7724-7738. DOI:10.1002/ejoc.201300847

Daďová J., Kümmel S., Feldmeier C., Cibulková J., Pažout R., Maixner J., Gschwind R. M., König B., Cibulka R.: Aggregation effects in visible light flavin photocatalysts: Synthesis, structure and catalytic activity of 10-arylflavins, Chem. Eur. J., 2013, 19, 1066-1075. DOI:10.1002/chem.201202488

2012

Hartman T., Herzig V., Buděšínský M., Jindřich J., Cibulka R., Kraus T.: Flavin-cyclodextrin conjugates: effect of the structure on catalytic activity in enantioselective sulfoxidations, Tetrahedron: Asymmetry, 2012, 23, 1571-1583. DOI:10.1016/j.tetasy.2012.10.017

Šturala J., Cibulka R.: Novel synthesis of symmetrical dinitro and diamino Tröger’s base analogues, Eur. J. Org. Chem., 2012, 7066-7074. DOI:10.1002/ejoc.201201188

Cibulka R., Jurok R.: ORGANOKATALYTICKÉ ENANTIOSELEKTIVNÍ OXIDACE SULFIDŮ NA SULFOXIDY, Chemické listy, 2012, 106, 896-902. http://www.chemicke-listy.cz/docs/full/2012_10_896-902.pdf

Ménová P., Cibulka R.: INSIGHT INTO THE CATALYTIC ACTIVITY OF ALLOXAZINIUM AND ISOALLOXAZINIUM SALTS IN THE OXIDATIONS OF SULFIDES AND AMINES WITH HYDROGEN PEROXIDE, J. Mol. Catal. A: Chemical, 2012, 363-364, 362-370. DOI:10.1016/j.molcata.2012.07.012

Daďová J., Svobodová E., Sikorski M., König B., Cibulka R.: Photooxidation of sulfides to sulfoxides mediated by tetra-O-acetylriboflavin and visible light. ChemCatChem, 2012, 4, 620-623. DOI:10.1002/cctc.201100372

Tisková zpráva:"Blue Light District: Sulfide Photooxidation" (ChemistryViews.org)

2011

Mojr V., Budesinsky M., Cibulka R., Kraus T.: Alloxazine-cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations. Org. Biomol. Chem., 2011, 9, 7257-7580. DOI:10.1039/C1OB05934C + Cover picture

Ménová P., Eigner V., Čejka J., Dvořáková H., Šanda M., Cibulka R.: Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles. J. Mol. Struct. 2011, 1004, 178-187. DOI:10.1016/j.molstruc.2011.08.002

Sayin S., Akkus G. U., Cibulka R., Stibor I., Yilmaz M: Synthesis of Flavin-Calix[4]arene Conjugate Derivatives. Helv. Chim. Acta 2011, 94, 481-485. DOI:10.1002/hlca.201000260

Ménová P., Kafka F., Dvořáková H., Gunnoo S., Šanda M., Cibulka R.: Pyrazinium Salts as Efficient Organocatalysts of Mild Oxidations with Hydrogen Peroxide. Adv. Synth. Catal. 2011, 353, 865-870. DOI:10.1002/adsc.201000906

2010

Rohlíček J. Cibulka R., Cibulková J., Maixner J., Hušák M.: 10-Methylisoalloxazine-5-oxide from synchrotron powder diffraction data. Acta Cryst. 2010, E66, o3350–o3351. DOI:10.1107/S1600536810048932

Mojr V., Herzig V., Budesinsky M., Cibulka R., Kraus T.: Flavin-cyclodextrin conjugates as catalysts of enantioselective sulfoxidations with hydrogen peroxide in aqueous media. Chem. Comm., 2010, 46, 7599–7601. DOI:10.1039/C0CC02562C

Kovaříček P., Eigner V., Holakovský R.: Ribbon and Pleated Sheet Formation by Anion-Directed Hydrogen Bonding In 1,4-Bis(4,5-dihydro-1H-imidazol-2-yl)benzene Salts.Structural Chemistry Communications, 2010, Vol. 1, No. 1, 8-11. http://www.factumpress.com/index.php/scc/article/viewFile/19/pdf

Jurok R., Cibulka R., Dvořáková H., Hampl F., Hodačová J.: Planar Chiral Flavinium Salts - Prospective Catalysts for Enantioselective Sulfoxidation Reactions. Eur. J. Org. Chem. 2010, 5217-5224. DOI:10.1002/ejoc.201000592

Cibulka R.: Flaviny – perspektivní katalyzátory oxidací a redukcí. Chem. Listy 2010,104, 326-333. http://chemicke-listy.cz/docs/full/2010_05_326-333.pdf

J. Budka, V. Eigner, R. Holakovský, P. Kovarícek and T. Louzilová: 25,26,27,28-Tetrapropoxycalix[4]arene-5,17-dicarbonitrile. Acta Cryst. 2010, E66, o419-o420. http://journals.iucr.org/e/issues/2010/02/00/om2307/om2307.pdf

Jiří Žurek, Radek Cibulka, Hana Dvořáková, Jiří Svoboda: N1,N10-Ethylene-bridged flavinium salts derived from L-valinol: synthesis and catalytic activity in H2O2oxidations, Tetrahedron Lett. 2010, 51, 1083-1086. DOI:10.1016/j.tetlet.2009.12.096

2009

Ménová P., Eigner V., Cibulka R., Čejka J., Dvořáková H.: 5-Ethyl-4a-methoxy-1,3-dimethyl-4a,5-dihydrobenzo[g]pteridine-2,4(1H,3H)dione. Acta Cryst. 2009, E65, o1536–o1537. DOI:10.1107/S1600536809020856

Cibulka R., Baxová L., Dvořáková H., Hampl F., Ménová P., Mojr V., Plancq B., Sayin S.: Catalytic effect of alloxazinium and isoalloxazinium salts on oxidation of sulfides with hydrogen peroxide in micellar media. Collect. Czech. Chem. Commun. 2009, 74, 973-993. DOI:10.1135/cccc2009030

2008

Jurok R., Svobodová E., Cibulka R.,Hampl F.: Reactivity in micelles - Are we really able to design micellar catalysts? Collect. Czech. Chem. Commun. 2008, 73, 127-146. DOI:10.1135/cccc20080127

2007

Baxová L., Cibulka R., Hampl F.: Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as terminal oxidant. J. Mol. Catal. A. 2007, 277, 53–60. DOI:10.1016/j.molcata.2007.07.027

Cibulka R., Svobodová E., König B., Ludvík J., Hampl F., Liška F.: Studium využití některých N-donorových ligandů a jejich komplexů s ionty přechodných kovů. Chem. Listy 2007, 101, 886-894. http://chemicke-listy.cz/docs/full/2007_11_886-894.pdf

2006

Celik H., Ekmekci G., Ludvík J., Pícha J., Zuman P: Electroreduction of aromatic oximes: Diprotonation, adsorption, imine formation, and substituent effects. J. Phys. Chem. B 2006, 110, 6785-6796. DOI:10.1021/jp056808t

Kivala M., Cibulka R., Hampl F.: Cleavage of 4-nitrophenyl diphenyl phosphate by isomeric quaternary pyridinium ketoximes - How can structure and lipophilicity of functional surfactants influence their reactivity in micelles and microemulsions?Collect. Czech. Chem. Commun. 2006, 71, 1642-1658. DOI:10.1135/cccc20061642

2005

Svobodová E., Cibulka R., Hampl F., Šmidrkal J., Liška F.: Metal ion transport through bulk liquid membrane mediated by cationic ligand surfactants. Collect. Czech. Chem. Commun. 2005, 70, 441-465. DOI:10.1135/cccc20050441

Chvapil M., Kielar F., Liška F., Šilhánková A., Bregel K.: Synthesis and evaluation of long-acting d-penicillamine derivatives. Connective Tissue Research 2005, 46, 242-250. DOI:10.1080/03008200500416690

Pícha J., Kuča K., Kivala M., Kohout M., Cabal J., Liška F.: A new group of monoquaternary reactivators of acetylcholinesterase inhibited by nerve agents. J. Enzyme Inhib. Med. Chem. 2005, 20, 233-237. DOI:10.1080/14756360400021858

2004

Pícha J., Cibulka R., Hampl F., Liška F., Pařík P., Pytela O.: Reactivity of p-substituted benzaldoximes in the cleavage of p-nitrophenyl acetate: kinetic and mechanism.Collect. Czech. Chem. Commun. 2004, 69, 397-413. DOI:10.1135/cccc20040397

Pícha J., Cibulka R., Liška F., Pařík P., Pytela O.: Reparametrization and/or determination of Hammett, inductive, mesomeric and AISE substituent constants for five substituents: N+(CH3)3, CH2N+(CH3)3, CH2Py, CH2SO2CH3 and PO(OCH3)2.Collect. Czech. Chem. Commun. 2004, 69, 2239-2252. DOI:10.1135/cccc20042239

Wiest O., Harrison C. B., Saettel N. J., Cibulka R., Sax M., König B.: Design, synthesis and evaluation of a biomimetic artificial photolyase model. J. Org. Chem. 2004, 69, 8183–8185. DOI:10.1021/jo0494329

Cibulka R., Vasold R. König B.: Catalytic Photooxidation of 4-Methoxybenzyl alcohol with Flavin Zinc(II) cyclen complex. Chem. Eur. J. 2004, 10, 6223–6231. DOI:10.1002/chem.200400232

2002

Ludvik J., Cibulka R.: Electroreduction of methyl azinyl ketoximes and their Ni(II), Cu(II) and Zn(II) complexes on mercury - correlation with their hydrolytic activity. Proceedings of the Fifth International Manuel M. Baizer Symposium in Honor of Professor Jean Michel Saveant, The 201th Meeting of the Electrochemical Society2002, Vol. 10, p. 142–146.

2001

Cibulka R., Císařová I., Ondráček J., Liška F., Ludvík J.: Electrochemical Reductions of Ni2+, Cu2+ and Zn2+ Complexes of Azinyl Methyl Ketoximes on Mercury. Collect. Czech. Chem. Commun. 2001, 66, 170. DOI:10.1135/cccc20010170

Kotoučová H., Cibulka R., Hampl F., Liška F.: Amphiphilic quaternary pyridinium ketoximes as functional hydrolytic micellar catalysts – does the nucleophilic function position influence their reactivity? J. Mol. Catal., 2001, 174, 59. DOI:10.1016/S1381-1169(01)00178-9

Mlíčková K., Šebela M., Cibulka R., Frébort I., Peč P., Liška F., Tanizawa K.: Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes. Biochimie 2001, 83(11-12), 995–1002. DOI:10.1016/S0300-9084(01)01345-1

Cibulka R., Hampl F., Kotoučová H., Páv O., Šilhánková A., Liška F.: Quaternary ketoximes – New perspective compounds for hydrolysis of toxic organophosphates.Vojenské zdrav. Listy – Suplementum- 2001, 70(1), 38–40.

Cibulka R.: Hydrolytické katalyzátory založené na komplexech alkyl(pyridin-2-yl)ketoximů. Chem. Listy 2001, 95, 809–810. http://chemicke-listy.cz/docs/full/archiv/2001/12-PDF/809-810.pdf

2000

Cibulka R., Hampl F., Kotoučová H., Mazáč J., Liška F.: Quaternary pyridinium ketoximes – New efficient micellar hydrolytic catalysts. Collect. Czech. Chem. Commun. 2000, 65, 227. DOI:10.1135/cccc20000227

Cibulka R., Liška F., Ludvík J.: Electrochemical reductions of methyl azinyl ketoximes on mercury. Collect. Czech. Chem. Commun. 2000, 65, 1630. DOI:10.1135/cccc20001630

1999

Cibulka R., Hampl F., Šmidrkal J. and Liška F.: Lipophilic N-[2-hydroxyimino-2-(pyridin-2-yl)ethyl]tialkylammonium salts – New ligands for metal ion extractions into organic solvents, Tetrahedron Lett. 1999, 40, 6849. DOI:10.1016/S0040-4039(99)01382-9

Cibulka R., Hampl F., Martinu T., Mazac J., Totevova S., Liska F.: Metal ion chelates of lipophilic alkyl diazinyl ketoximes as hydrolytic catalysts Collect. Czech. Chem. Commun. 1999, 64, 1159. DOI:10.1135/cccc19991159

1998

Cibulka R., Hampl F., Liška F.: Příprava a využití amfifilních oximů odvozených od azinů, Chem. listy 1998, 92(6), 469. http://chemicke-listy.cz/docs/full/1998_06_469-474.pdf

Kotoučová H., Mazáč J., Cibulka R., Hampl F. and Liška F: Unusual course of the p-nitrophenyl phosphate esters cleavage by 3-hydroxyiminoalkylpyridinium salts in micellar solutions, Chem. Lett. 1998 (7), 649. DOI:10.1246/cl.1998.649

1997

Cibulka R., Dvořák D., Hampl F., Liška F.: Metallomicellar hydrolytic catalysts containing ligand surfactants derived from alkyl-2-pyridinylketoxime, Collect. Czech. Chem. Commun. 1997, 62, 1342. DOI:10.1135/cccc19971342

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Current group members

Students:      

PhD students:      

Assoc. Prof.:

Jiří Lapčík Peter Polák Tomáš Tobrman
Marek Čubiňák Hana Váňová  
Eliška Fikejzová  

Technician:

Filip Gracias    Marta Tokárová
Roman Valeš     
Václav Vraštil    
Petr Oeser    
Jakub Koudelka    


Our alumni:

 

PhD students: Master students: Bachelor students:
  • Vladislav Kotek (2015)
  • Martin Křováček (2011)
  • Tomáš Tobrman (2005)
  • Luděk Meca (2004)
  • Martina Havelková (2002)
  • Miroslav Havránek (1998)
  • Kristýna Kolouchová (2016)
  • Lukáš Lattenberk (2016)
  • Iegor Vyshnytskyi (2016)
  • Peter Polák (2015)
  • Hana Váňová (2015)
  • Petr Koukal (2013)
  • Ivana Jurásková (2012)
  • Ivana Nousková (2011)
  • Ivana Kubíčková (2011)
  • Petra Slavíková (2009)
  • Markéta Šmídková (2009)
  • Miroslava Tobrmanová (2007)
  • Jaroslav Padevět (2006)
  • Jana Roháčová (2005)
  • Jiří Černý (2002)
  • Dušan Drahoňovský (2000)
  • Ivan Rotrekl (2000)
  • Martin Studenovský (1999)
  • Petr Suchý (1996)
  • Roman Wágner (1995)
  • Marek Čubiňák (2016)
  • Eliška Fikejzová (2016)
  • Lukáš Lattenberk (2014)
  • Hana Váňová (2013)
  • Peter Polák (2013)
  • Michal Maryška (2012)
  • Šárka Pěchoučková (2011)
  • Gabriel Tóth (2008)

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2016

  • Vanova, H.; Tobrman, T.; Hoskovcova, I.; Dvorak, D.:
    Modular synthesis of Fischer biscarbene complexes of chromium
    Organometallics 2016, 35, 2999-3006 DOI:10.1021/acs.organomet.6b00527

  • Kotek, V.; Polák, P.; Dvořáková, H.; Tobrman, T.:
    Aluminium Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues
    Eur. J. Org. Chem. 2016, 5037-5044 DOI:10.1002/ejoc.201600959

  • Polák, P.; Váňová, H.; Dvořák, D.; Tobrman, T.:
    Recent Progress in Transition Metal-Catalyzed Stereoselective Synthesis of Acyclic All-Carbon Tetrasubstituted Alkenes
    Tetrahedron Lett. 2016, 57, 3684-3693 DOI:10.1016/j.tetlet.2016.07.030 

  • Kotek, V.; Polák, P.; Tobrman, T.
    Efficient and Simple Preparation of Functionalized 1,1-Dibromoenol Phosphates
     
    Monatshefte fuer Chemie 2016, 147, 405-412 DOI:10.1007/s00706-015-1613-6


2015

 

2014

 

2013

 

2012

 

2011

 

2010

  

2009-1996

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Group_photo_2018_10

Group Leader:                  Assoc. Prof. Jana Hodačová

 

Technician:                       Michal Shejbal

 

Students:                           MSc. David Tetour (PhD student)

                                               Bc. Jaroslava Šimoniková (Master student)

                                               Bc. Nikola Vršek (Master student)

                                               Bc. Océane Baffroy (Master student)

                                              Jindřich Kropáček (Bachelor student)

                                              Patrik Šobr (Bachelor student)

                                              

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Selected publications:

Bím, D.; Svobodová, E.; Eigner, V.; Rulíšek, L.; Hodačová, J. Chem.  Eur. J. 2016, 22, 10426-10437.  Copper(II) and Zinc(II) Complexes of Conformationally Constrained Polyazamacrocycles as Efficient Catalysts for RNA Model Substrate Cleavage in Aqueous Solution at Physiological pH

Nunes, S. C.; Bürglová, K.; Hodačová, J.; Ferreira, R. A. S.; Carlos, L. D.; Almeida, P.; Cattoën, X.; Wong Chi Man, M.; de Zea Bermudez, V. C., Eur. J. Inorg. Chem. 2015, No.7, 1218-1225. Nanostructuring of Bridged Organosilane Precursors with Pendant Alkyl Chains.

Pazderová, M.; Profant, V.; Seidlerová, B.; Dlouhá, H.; Hodačová, J.; Jávorfi, T.; Siligardi, G.; Baumbruk, V.; Bednárová, L.; Maloň, P., J. Phys. Chem. B 2014, 118, 11100-11108. Electronic Circular Dichroism of the Chiral Rigid Tricyclic Dilactam with Nonplanar Tertiary Amide Groups.

Bürglová, K.; Noureddine, A.; Hodačová, J.; Toquer, G.; Cattoën, X.; Wong Chi Man, M., Chem. Eur. J. 2014, 20, No. 33, 10371-10382. A General Method for Preparing Bridged Organosilanes with Pendant Functional Groups and Functional Mesoporous Organosilicas.

Cattoën, X.; Noureddine, A.; Croissant, J.; Moitra, N.; Bürglová, K.; Hodačová, J.; de los Cobos, O.; Lejeune, M.; Rossignol, F.; Toulemon, D.; Bégin-Colin, S.; Pichon, B. P.; Raehm, L.; Durand, J.-O.; Wong Chi Man, M., J. Sol-Gel Sci. Technol. 2014, 70, No. 2, 245-253. Click Approaches in Sol-Gel Chemistry.

Wong Chi Man, M.; Cattoën, X.; Moitra, N.; Hodačová, J.; Bürglová, K., Patent EP2870165 (13.05.2015). Functionalisable polysilylated organosilane precursors.             

Wong Chi Man, M.; Cattoën, X.; Hodačová, J.; Bürglová, K., Patent EP2882758 (17.06.2015). Polysilylated organosilane compounds.

Bürglová, K.; Moitra, N.; Hodačová, J.; Cattoën, X.; Wong Chi Man, M., J. Org. Chem. 2011, 76, No. 18, 7326-7333. Click Approaches to Functional Water-Sensitive Organotriethoxysilanes.

Hlinka, J.; Hodačová, J.; Raehm, L.; Granier, M.; Ramonda, M.; Durand, J.-O., C. R. Chimie 2010, 13, 481-485. Attachment of trianglamines  to silicon wafers, chiral recognition by chemical force microscopy.

Hodačová, J.; Buděšínský, M., Org. Lett. 2007, 9, 5641-5643. New Synthetic Path to 2,2´-Bipyridine-5,5´-dicarbaldehyde and its Use in the [3+3] Cyclocondensation with trans-1,2-Diaminocyclohexane.

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Smart organic materials group

Kohout people 2020_05

The web page is currently under construction. Please check for updates.

Contacts

Prof. Jiří Svoboda

building A, room 278e

+ 420 220 44 3688

Jiri.Svoboda@vscht.cz

Dr. Václav Kozmík

building A, room 308b

+ 420 220 44 4118

Vaclav.Kozmik@vscht.cz

Assoc. Prof. Michal Kohout

building A, rooms 278e/308b

+ 420 220 44 3688/4118

Michal.Kohout@vscht.cz

 
   
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People

Employees:

  • Assoc. Prof. Michal Kohout
  • Prof. Jiří Svoboda 
  • Dr. Václav Kozmík
  • Markéta Slabochová, MSc.

Ph.D. students:

  • Anna Poryvai, MSc.
  • Jana Herciková, MSc.
  • Michal Šmahel, MSc.
  • Tereza Černá, MSc.
  • Natalie Kolderová, MSc.
  • Martin Paškan , MSc.

Students:

  • Barbora Jansová
  • Žaneta Javorská
  • Pavel Mata
  • Jakub Kňava
  • Diana Jágerová
  • Anežka Kuncová
  • Magdalena Labíková
  • Jakub Dávid Malina
  • Anna Rejzková 
  • Petr Bečvář 
  • Silvie Fabiánová
  • Marie Kloubcová
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Research topics

Photosensitive liquid crystals

Magnetic liquid crystals

Chiral liquid crystals

Novel chiral ion exchangers

Chiral separation

Biologically active substances

Continuous flow organocatalysis



Current Special Issues guest-edited by group members

Photosensitive Liquid Crystals

https://www.mdpi.com/journal/crystals/special_issues/photosensitive_liquid_crystals

Chiral Separation by Liquid Chromatography

https://www.mdpi.com/journal/separations/special_issues/chiral_chromatography



Photosensitive liquid crystals

Light Tunable Gratings Based on Flexoelectric Effect in Photoresponsive Bent‐Core Nematics

A new photoresponsive bent‐core nematic (BCN) material, which exhibits flexoelectric domains (FDs) driven by electric field, is reported. Unexpectedly, it is found that the morphologies of FDs can be controlled by irradiation with light fields. This light tunability is ascribed to the photoisomerization effect of the azo moiety within the BCN molecules, where the ratio of trans and cis isomers changes according to the parameters of the light field, resulting in adjustable electric threshold and periodicity of FDs. Based on this principle, a prototype of controllable optical grating is assembled, whose operation can be manipulated by the wavelength or intensity of light. Due to the easy, instant, and remote operation by light, this optical, contactless tunability has a great advantage over traditional electric control in tunable photonic devices.

Picture1

Jing H. et al. Adv. Opt. Mater. 2019, 7, 1801790. https://doi.org/10.1002/adom.201801790



Magnetic liquid crystals

All-organic liquid crystalline radicals with a spin unit in the outer position of a bent-core system

All-organic paramagnetic liquid crystals offer the advantage of a long-range order of liquid crystalline phases and the magnetic properties of the individual molecules. In such systems, the magnetic properties can be modified by phase transition or the application of external fields. This manuscript reports on paramagnetic all-organic bent-core liquid crystals having the radical-bearing unit (TEMPO) in the terminal position of an elongating side arm. The mesomorphic properties of the materials are ensured by the optimized molecular structure. The paramagnetic nature of the mesogenic materials is investigated by electron paramagnetic resonance, the magnetic properties of the bulk materials are studied by SQUID magnetometry. It is shown that the materials preserve their magnetic properties within the whole temperature range of liquid crystalline behaviour. Moreover, a strong correlation between spin orientation and molecular alignment within different mesophases has been observed, however, SQUID measurements do not provide evidence about spin glass formation. Unlike materials presented thus far, the position of the spin unit has a plausible effect on the formation of mesophases leading to unique polymorphism of the studied paramagnetic compounds. For two six-ring hockey-stick-like compounds, polymorphism with four different mesophases, including two B1Rev-type phases, has been found in a broad temperature range (about 20 °C each). Thus, for the first time, such behaviour is described for all-organic paramagnetic bent-core liquid crystals.

Bajzíková K. et al. J. Mater. Chem. C, 2016, 4, 11540-11547. https://doi.org/10.1039/C6TC04346A



Chiral liquid crystals

The effect of the length of terminal n-alkyl carboxylate chain on selfassembling and photosensitive properties of chiral lactic acid derivatives

A new series of photosensitive azo materials possessing a chiral alkyl lactate moiety and terminal n-alkyl carboxylate unit close to the azo group has been synthesized and studied. The length of the n-alkyl carboxylate chain has been systematically varied in order to establish the effect of the molecular structure on the self-assembling behaviour. Two series of materials possessing hexyl and dodecyl alkyl chains in the chiral part of the molecule have been studied. It has been shown that the length of both the alkyl chains strongly influences the mesomorphic behaviour, however, each chiral/achiral chain has different utility to tune the mesomorphic properties. With exception of the compound with the longest chains, all studied compounds exhibited the chiral tilted ferroelectric smectic C* phase. Based on the combination of terminal alkyl chains, chiral nematic, orthogonal smectic A*, and twist grain boundary smectic A* phases have been detected on cooling beyond the SmC* phase. The presence of the photosensitive functional N=N group in the molecular core allowed further tuning of the material properties by UV light illumination. The E-to-Z photoisomerization of the azo group and subsequent thermal back-isomerisation have been studied in solution by nuclear magnetic resonance and most importantly in the mesophases on bulk samples. We report on UV-induced isothermal switching from chiral smectic and nematic mesophases into the isotropic phase, respectively, and differences in the textures of mesophase upon restoration of the ordered liquid.

Poryvai A. et al. J. Mol. Liq. 2019, 275, 829-838. https://doi.org/10.1016/j.molliq.2018.11.058



Novel chiral ion-exchangers

Strong cation exchange-type chiral stationary phase for enantioseparation of chiral amines in subcritical fluid chromatography

A new strong cation exchange type chiral stationary phase (SCX CSP) based on a syringic acid amide derivative of trans-(RR)-2-aminocyclohexanesulfonic acid was applied to subcritical fluid chromatography (SFC) for separation of various chiral basic drugs and their analogues. Mobile phase systems consisting of aliphatic alcohols as polar modifiers and a broad range of amines with different substitution patterns and lipophilicity were employed to evaluate the impact on the SFC retention and selectivity characteristics. The observed results point to the existence of carbonic and carbamic acid salts formed as a consequence of reactions occurring between carbon dioxide, the alcoholic modifiers and the amine species present in the sub/supercritical fluid medium, respectively. Evidence is provided that these species are essential for affecting ion exchange between the strongly acidic chiral selector units and the basic analytes, following the well-established stoichiometric displacement mechanisms. Specific trends were observed when different types of amines were used as basic additives. While ammonia gave rise to the formation of the most strongly eluting carbonic and carbamic salt species, simple tertiary amines consistently provided superior levels of enantioselectivity. Furthermore, trends in the chiral SFC separation characteristics were investigated by the systematic variation of the modifier content and temperature. Different effects of additives are interpreted in terms of changes in the relative concentration of the transient ionic species contributing to analyte elution, with ammonia-derived carbamic salts being depleted at elevated temperatures by decomposition. Additionally, in an effort to optimize SFC enantiomer separation conditions for selected analytes, the impact of the type of the organic modifier, temperature, flow rate and active back pressure were also investigated.

Wolrab D. et al. J. Chromatogr. A 2013, 1289, 94-104. https://doi.org/10.1016/j.chroma.2013.03.018



Chiral separation

Consequences of transition from liquid chromatography to supercritical fluid chromatography on the overall performance of a chiral zwitterionic ion-exchanger

Major differences in the chromatographic performance of a zwitterion ion-exchange type (ZWIX) chiral stationary phase (CSP) in supercritical fluid chromatography (SFC) and high-performance liquid chromatography (HPLC) have been observed. To explain these differences, transition from HPLC to SFC conditions has been performed. The amount of a protic organic modifier in supercritical carbon dioxide (scCO2) was stepwise increased and the effect of this change studied using acidic, basic and ampholytic analytes. At the same time, the effect of various basic additives to the mobile phase and transient acidic buffer species, formed by the reaction of scCO2 with the organic modifier and additives, was assessed. Evidence is provided that a transient acid together with the intrinsic counter-ions present in the ZWIX selector structure drive the elution of analytes even when no buffer is employed. We show that the tested analytes can be enantioseparated under both SFC and HPLC conditions; the best conditions for the resolution of ampholytes are in the so-called enhanced-fluidity mobile phase region. As a consequence, subcritical fluid and enhanced-fluidity mobile phase regions seem to be chromatographic modes with a high potential for operating ZWIX CSPs.

Picture2

Wolrab D. et al. J. Chromatogr. A 2017, 1517, 165-175. https://doi.org/10.1016/j.chroma.2017.08.022



Biologically active substances

Synthesis, absolute configuration and in vitro cytotoxicity of deschloroketamine enantiomers: rediscovered and abused dissociative anaesthetic

In this study, we aim to determine differences in cytotoxicity of racemic deschloroketamine and its enantiomers. The synthesized racemate of this recently rediscovered and abused dissociative anaesthetic was resolved by chiral HPLC and the absolute configuration of the enantiomers was assigned using a combination of circular dichroism methods and single-crystal X-ray. Not only the absolute configuration, but also the most preferred conformers present in the crystal were successfully determined by electron and vibrational circular dichroism supported by ab initio calculations, and confirmed by X-ray. The in vitro cytotoxicity of racemic deschloroketamine and its enantiomers was determined for nine different types of cell lines. Generally, (S)-deschloroketamine exhibited higher cytotoxicity in the majority of cases. For human embryonic kidney cells (HEK 293T), the (S)-enantiomer reached the IC50 below 1 mM concentration and, in consequence, proved to be twice as potent as the (R)-enantiomer. On the other hand, live-cell fluorescence microscopy imaging at sub-IC50 concentrations provided evidence for only a minor effect of deschloroketamine racemate and enantiomers on endoplasmic reticulum stress and mitochondria morphology in neuroblastoma cells SH-SY5Y.

Picture3

Jurásek B. et al. New J. Chem., 2018, 42, 19360-19368. https://doi.org/10.1039/C8NJ03107J



Continuous flow organocatalysis

Silica gel-immobilized multidisciplinary materials applicable in stereoselective organocatalysis and HPLC separation

In this pilot study, we present novel bifunctional silica gel-immobilized materials applicable as heterogeneous organocatalysts and stationary phases in HPLC. The materials provided high stereoselectivity in both batch and continuous flow catalysis of a model Michael addition (cyclohexanone to (E)-β-nitrostyrene). In the batch reaction, the catalysts proved their sustainable catalytic activity over five consecutive recycling experiments. Under continuous flow reaction conditions, the catalytic activity was found to be superior to the batch reaction, and moreover, the same immobilized materials were utilized as stationary phases in HPLC showing very good chemoselective separation of model acidic analytes.

Picture4

Tůma J. et al. RSC Adv., 2018, 8, 1174-1181. https://doi.org/10.1039/C7RA12658A

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Patent

Gaálová, F. Yalcinkaya, P. Cuřínová, M. Kohout, I. Stibor, P. Izák: Kompozitní chirální membrána, způsob její přípravy a způsob obohacování směsí enantiomerů, číslo patentu: 308513, datum udělení: 2.9.2020.

Publications 2023

  1. Jurásek, B.; Fagan, P.; Dolenský, B.; Paškanová, N.; Dobšíková, K.; Raich, I.; Jurok, R.; Setnička, V.; Kohout, M.; Čejka, J.; Kuchař, M. A structural spectroscopic study of dissociative anaesthetic methoxphenidine. New J. Chem. 2023, 47, 4543.
    https://doi.org/10.1039/d2nj06126k

  2. Dobšíková, K.; Javorská, Ž.; Paškan, M.; Spálovská, D.; Trembuláková, P.; Herciková, J.; Kuchař, M.; Kozmík, V.; Kohout, M.; Setnička, V. Enantioseparation and a comprehensive spectroscopic analysis of novel synthetic cathinones laterally substituted with a trifluoromethyl group. Spectrochim. Acta, Part A, 2023, 291, 122320.
    https://doi.org/10.1016/j.saa.2023.122320

Publications 2022

  1. Paškan, M.; Rimpelová, S.; Svobodová Pavlíčková, V.; Spálovská, D.; Setnička, V.; Kuchař, M.; Kohout, M.: 4-Isobutylmethcathinone—A novel synthetic cathinone with high in vitro cytotoxicity and strong receptor binding preference of enantiomers. Pharmaceuticals 2022, 15, 1495.
    https://doi.org/10.3390/ph15121495

  2. Poryvai, A.; Šmahel, M.; Švecová, M.; Nemati, A.; Shadpour, S.; Ulbrich, P.; Ogolla, T.; Liu, J.; Novotná, V.; Veverka, M.; Vejpravová J.; Hegmann, T.; Kohout, M.: Chiral, magnetic, and photosensitive liquid crystalline nanocomposites based on multifunctional nanoparticles and achiral liquid crystals. ACS Nano, 2022, 16, 11833.-11841.
    https://doi.org/10.1021/acsnano.1c10594

  3. Hao, L.; Jing, H.; Xiang, Y.; Iljin, A.; Wang, Y.; Li, H.; Li, Q.; Peng, J.; Kohout, M.: Transient optically induced grating and underlying transport process in bent-core nematics. J. Appl. Phys. 2022, 132, 065108.
    https://doi.org/10.1063/5.0096106

  4. Sysel, P.; Hovorka, Š.; Kohout, M.; Holakovský, R.; Žádný, J.; Čížek, J.; Izák, P. Optically active polyimides with different thermal histories of their preparation. Chirality 2022, 34, 1151-1161.
    https://doi.org/10.1002/chir.23476

  5. Asnin, L.; Herciková, J.; Lindner, W.; Klimova, Y.; Ziganshina, D.; Reshetova, E.; Kohout, M.: Chiral separation of dipeptides on Cinchona-based zwitterionic chiral stationary phases under buffer-free reversed-phase conditions. Chirality 2022, 34, 1065-1077.
    https://doi.org/10.1002/chir.23471

  6. Malinčík, J.; Kohout, M.; Svoboda, J.; Stulov, S.; Pociecha, D.; Böhmová, Z.; Novotná, V. Photochromic spiropyran-based liquid crystals. J. Mol. Liq. 2022, 346, 117842.
    https://doi.org/10.1016/j.molliq.2021.117842

  7. Muraveva, V.; Kozmík, V.; Kohout, M.; Manko, A.; Piryazev, A.; Ivanov, D.; Abramchuk, S.; Cigl, M.; Bobrovsky, A. The smectogenicity as a crucial factor of broadening of the selective light reflection peak in cholesteric photopolymerizable mixtures. Liq. Cryst. 2022, 49, 1459-1465.
    https://doi.org/10.1080/02678292.2022.2041745

  8. Štefková-Mazochová, K.; Danda, H.; Dehaen, W.; Jurásek, B.; Šíchová, K.; Pinterová-Leca, N.; Mazoch, V.; Krausová, B.H.; Kysilov, B.; Smejkalová, T.; Vyklický, L.; Kohout, M.; Hájková, K.; Svozil, D.; Horsley, R.R.; Kuchař, M.; Páleníček, T.: Pharmacokinetic, pharmacodynamic, and behavioural studies of deschloroketamine in Wistar rats. Br. J. Pharmacol. 2022, 179, 65-83.

Publications 2021

  1. Shruthi, S.; Smahel, M.; Kohout, M.; Shanker, G.; Hegde, G.:
    Influence of linking units on the photo responsive studies of azobenzene liquid Crystals: Application in optical storage devices 
    J. Mol. Liq. 2021, 339, 116744 DOI:10.1016/j.molliq.2021.116744

  2. Skopalová H., Kozmík V., Šmahel M., Svoboda J., Pacherová O., Kohout M. Mesomorphic properties of non-symmetric bent-core liquid crystals with a lateral substituent in the apex position. Liq. Cryst. 2021, 48, 1010-1024
    https://doi.org/10.1080/02678292.2020.1836567

  3. Cigl M., Hampl F., Svoboda J., Podoliak N., Stulov S., Kohout M., Novotná V. Laterally substituted biphenyl benzoates – synthesis and mesomorphic properties. Liq. Cryst. 2021, 48, 526-536
    https://doi.org/10.1080/02678292.2020.1794069

  4. Spálovská D., Paškan M., Jurásek B., Kuchař M., Kohout M., Setnička V. Structural spectroscopic study of enantiomerically pure synthetic cathinones and their major metabolites, New J. Chem. 2021, 45, 850.
    https://doi.org/10.1039/D0NJ05065B

  5. Wolrab D., Frühauf P., Kolderová N., Kohout M. Strong cation- and zwitterion-exchange-type mixed-mode stationary phases for separation of pharmaceuticals and biogenic amines in different chromatographic modes. J. Chromatogr. A 2021, 1635, 461751.
    https://doi.org/10.1016/j.chroma.2020.461751

  6.  Jágerová, D.; Šmahel, M.; Poryvai, A.; Macháček, J.; Novotná, V.; Kohout, M.: Photosensitive bent-core liquid crystals with laterally substituted azobenzene unit. Crystals, 2021, 11, 1265.
    https://doi.org/10.3390/cryst11101265

  7. Karongo, R.; Ge, M.; Horak, J.; Gross, H.; Kohout, M.; Lindner, W.; Lämmerhofer, M.: Rapid enantioselective amino acid analysis by ultra-high performance liquid chromatography-mass spectrometry combining 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate derivatization with core-shell quinine carbamate anion exchanger separation. J. Chromatogr. Open, 2021, 1, 100004.
    https://doi.org/10.1016/j.jcoa.2021.100004

  8. Herciková, J.; Spálovská, D.; Frühauf, P.; Izák, P.; Lindner, W.; Kohout, M.: Design and synthesis of naphthalene-based chiral strong cations exchangers and their application for chiral separation of basic drugs. J. Sep. Sci., 2021, 44, 3348-3356. DOI: 10.1002/jssc.202100127

Publications 2020

  1. Poryvai A., Bubnov A., Kohout M. Chiral Photoresponsive Liquid Crystalline Materials Derived from Cyanoazobenzene Central Core: Effect of UV Light Illumination on Mesomorphic Behavior. Crystals 2020, 10, 1161.
    https://doi.org/10.3390/cryst10121161

  2. Tlustý M., Spálovská D., Kohout M., Eigner V., Lhoták P. Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes. Chem. Commun. 2020, 56, 12773.
    https://doi.org/10.1039/D0CC05352J

  3. Skopalová H., Špaček P., Kozmík V., Svoboda J., Novotná V., Pociecha D., Kohout M. The Role of Substitution in the Apex Position of the Bent-Core on Mesomorphic Properties of New Series of Liquid Crystalline Materials. Crystals, 2020, 10, 735. https://doi.org/10.3390/cryst10090735

  4. Guselnikova O., Postnikov P., Kolská Z., Záruba K., Kohout M., Elashnikov R., Švorčík V., Lyutakov O. Homochiral metal-organic frameworks functionalized SERS substrate for atto-molar enantio-selective detection. Appl. Mater. Today 2020, 20, 100666.
    https://doi.org/10.1016/j.apmt.2020.100666

  5. Kolderová N., Jurásek B., Kuchař M., Lindner W., Kohout M. Gradient supercritical fluid chromatography coupled to mass spectrometry with a gradient flow of make-up solvent for enantioseparation of cathinones. J. Chromatogr. A 2020, 1625, 461286. https://doi.org/10.1016/j.chroma.2020.461286

  6. Tlustý M., Dvořáková H., Čejka J., Kohout M., Lhoták P. Regioselective Formation of Quinazoline Moiety on the Upper Rim of Calix[4]arene as the Way to Inherently Chiral Systems. New J. Chem. 2020, 44, 6490.
    https://doi.org/10.1039/D0NJ01035A

  7. Šmahel M., Poryvai A., Xiang Y., Pociecha D., Troha T., Novotná V., Svoboda J., Kohout M. Photosensitive bent-core nematic liquid crystals with various linking units in the side arms: Structure-properties relationships. J. Mol. Liq. 2020, 306, 112743. https://doi.org/10.1016/j.molliq.2020.112743

  8. Cigl M., Jurok R., Hampl F., Svoboda J., Podoliak N., Novotná V.: Lateral substituted phenyl biphenylcarboxylates ‒ non-chiral analogues of ferroelectric liquid crystals. Liq.  Cryst. 2020, 47, 768-776.
    https://doi.org/10.1080/02678292.2019.1679903

  9. Gaálová J., Yalcinkaya F., Cuřínová P., Kohout M., Yalcinkaya B., Koštejn M., Jirsák J., Stibor I., Bara J. E., Van der Bruggen B., Izák P. Separation of racemic compound by nanofibrous composite membranes with chiral selector. J. Membr. Sci. 2020, 596, 117728.
    https://doi.org/10.1016/j.memsci.2019.117728

  10. Otmar M., Gaálová J., Žitka J., Brožová L., Cuřínová P., Kohout M., Hovorka Š., Bara J. E., Van der Bruggen B., Jirsák J., Izák P. Preparation of PSEBS membranes bearing (S)-(-)-methylbenzylamine as chiral selector. Eur. Polym. J. 2020, 122, 109381. https://doi.org/10.1016/j.eurpolymj.2019.109381

Publications 2019

  1. Jing, H.; Xu, M.; Xiang, Y.; Wang, E.; Liu, D.; Poryvai, A.; Kohout, M.; Éber, N.; Buka, A.: Light tunable gratings based on flexoelectric effect in photoresponsive bent-core nematics. Adv. Opt. Mater. 2019, 1801790.
    https://doi.org/10.1002/adom.201801790

  2. Pokluda, A.; Kohout, M.; Chudoba, J.; Krupička, M.; Cibulka, R.: Nitrosobenzene: Reagent for the Mitsunobu esterification reaction. ACS Omega 2019, 4, 5012-5018.
    https://doi.org/10.1021/acsomega.8b03551

  3. Spálovská, D.; Maříková, T.; Kohout, M.; Králík, F.; Kuchař, M.; Setnička, V.: Methylone and pentylone: Structural analysis of new psychoactive substances. Forensic Toxicol. 2019, 37, 366-377.
    https://doi.org/10.1007/s11419-019-00468-z

  4. Poryvai, A.; Bubnov, A.; Pociecha, D.; Svoboda, J.; Kohout, M.: The effect of the length of terminal n-alkyl carboxylate chain of self-assembling and photosensitive properties of chiral lactic acid derivatives. J. Mol. Liq. 2019, 275, 829-838.
    https://doi.org/10.1016/j.molliq.2018.11.058

  5. Geibel, C.; Dittrich, K.; Woiwode, U.; Kohout, M.; Zhang, T.; Lindner, W.; Lämmerhofer, M.: Evaluation of superficially porous particle based zwitterionic chiral ion exchangers against fully porous particle benchmarks for enantioselective ultra-high performance liquid chromatography. J. Chromatogr. A 2019, 1603, 130-140.
    https://doi.org/10.1016/j.chroma.2019.06.026

  6. Poryvai, A.; Vojtylová-Jurkovičová, T.; Šmahel, M.; Kolderová, N.; Tomášková, P.; Sýkora, D.; Kohout, M.: Determination of optical purity of lactic acid-based chiral liquid crystals and corresponding building blocks by chiral high-performance liquid chromatography and supercritical fluid chromatography. Molecules 2019, 24, 1099.
    10.3390/molecules24061099

  7. Tlustý, M.; Eigner, V.; Babor, M.; Kohout, M.; Lhoták, P.: Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds. RSC Adv. 2019, 9, 22017-22030.
    https://doi.org/10.1039/C9RA05075B

  8. Horčic, M.; Svoboda, J.; Novotná, V.; Pociecha, D.: W-shaped mesogens and variations of their molecular structure. Liq. Cryst. 2019, 46, 816-824.
    https://doi.org/10.1080/02678292.2019.1573328

  9. Cigl, M.; Jurok, R.; Hampl, F.; Svoboda, J.; Podoliak, N.; Novotná, V.: Lateral substituted phenyl biphenylcarboxylates – non-chiral analogues of ferroelectric liquid crystals. Liq. Cryst. 2019.
    https://doi.org/10.1080/02678292.2019.1679903

  10. Kohout, M.; Hovorka, Š.; Herciková, J.; Wilk, M.; Sysel, P.; Izák, P.; Bartůněk, V.; von Baeckmann, C.; Pícha, J.; Frühauf, P.: Evaluation of silica from different vendors as the solid support of anion-exchange chiral stationary phases by means of preferential sorption and liquid chromatography. J. Sep. Sci. 2019, 42, 3653-3661.
    https://doi.org/10.1002/jssc.201900731

Publications 2018

  1. Jurásek, B.; Králík, F.; Rimpelová S.; Čejka, J.; Setnička, V.; Ruml, T.; Kuchař, M.; Kohout, M.:Synthesis, Absolute Configuration and in vitroCytotoxicity of Deschloroketamine Enantiomers: Rediscovered and Abused Dissociative Anaesthetic
    J. Chem. 201842, 19360-19368 DOI: 10.1039/c8nj03107j

  2. Landovsky, T.; Dvorakova, H.; Eigner, V.; Babor, M.; Krupicka, M.; Kohout, M.; Lhotak, P.:Chemoselective Oxidation of Phenoxathiin-based Thiacalix[4]arene and the Stereoselective Alkylation of Products
    New J. Chem.201842, 20074-20086 DOI: 1039/C8NJ04690E

  3. Schmitt, K.; Woiwode, U.; Kohout, M.; Zhang, T.; Lindner, W.; Lämmerhofer, M.:
    Comparison of small size fully porous particles and superficially porous particles of chiral anion-exchange type stationary phases in ultra-high performance liquid chromatography: effect of particle and pore size on chromatographic efficiency and kinetic performance
    Chromatogr. A20181569, 149-159 DOI:10.1016/j.chroma.2018.07.056

  4.  Spálovská, D.; Kralik, F.; Kohout, M.; Jurasek, B.; Habartová, L.; Kuchar, M.; Setnicka, V.: Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies 
    Chirality201830, 548-559 DOI:1002/chir.22825

  5. Wolrab, D.; Kohout, M.: Multimodální stacionární fáze pro kapalinovou chromatografii, způsob jejich přípravy a jejich použití. Národní patent č. 307339, číslo přihlášky 2017-193, datum udělení 2.5.2018, datum zveřejnění 13.6.2018.

  6. Kohout, M.; Wernisch, S.; Tuma, J.; Hettegger, H.; Picha, J.; Lindner W.: Effect of different immobilization strategies on chiral recognition properties of Cinchona-based anion exchangers 
    Sep. Sci.201841, 1355-1364 DOI:10.1002/jssc.201701213

  7. Bajtai, A.; Fekete, B.; Palkó, M.; Fülöp, F.; Lindner, W.; Kohout, M.; Ilisz, I.; Péter, A.:  Comparative study on the liquid chromatographic enantioseparation of cyclic β-amino acids and the related cyclic β-aminohydroxamic acids on Cinchona alkaloid-based zwitterionic chiral stationary phases 
    Sep. Sci.201841, 1216-1223 DOI:10.1002/jssc.201701190

  8. Sardella, R.; Macchiarulo, A.; Urbinati, F.; Ianni, F.; Carotti, A.; Kohout, M.; Lindner, W.; Péter, A.; Ilisz, I.: Exploring the enantiorecognition mechanism of Cinchona alkaloid-based zwitterionic chiral stationary phases and the basic trans-paroxetine enantiomers 
    Sep. Sci.201841, 1199-1207 DOI:10.1002/jssc.201701068

  9. Tuma, J.; Kohout, M.: Silica gel-immobilized multidisciplinary materials applicable in stereoselective organocatalysis and HPLC separation 
    RSC Adv.20188, 1174-1181 DOI:1039/c7ra12658a

  10. Kozmik, V.; Rodinová, E.; Prausová, T.; Svoboda, J.; Novotná, V.; Pociecha, D.: Mesogens with central naphthalene core substituted at various positions 
    Cryst. 2018, 45, 744-756 DOI: 10.1080/02678292.2017.1380238

  11. Bajzíková, K.; Vesely, J.; Kozmik, V.; Svoboda, J.; Novotná, V.; Pociecha, D.: Thiophene central core for the design of bent-shaped liquid crystals 
    Mol. Liq. 2018267, 496-503 DOI:10.1016/j.molliq.2018.02.009

  12. Horcic, M.; Svoboda, J.; Novotná, V.; Pociecha, D.; Gorecka, E.: Bent-core dimers with top-to-bottom linkage between central units 
    RSC Adv. 20188, 22974-22985 DOI: 1039/c8ra04108c

  13. Marz, M.; Kohout, M.; Nevesely, T.; Chudoba, J.; Prukala, D.; Nizinski, S.; Sikorski, M.; Burdzinski, G.; Cibulka, R.:Azodicarboxylate-free esterification with triphenylphosphine mediated by flavin and visible light: method development and stereoselectivity control
    Biomol. Chem.201816, 6809-6817 DOI:10.1039/C8OB01822G

 

Publications 2017

  1. Maixner, J.; Jurásek, B.; Kohout, M.; Kuchar, M.; Kacer, P.: X-ray powder diffraction data for (S)-Deschloroketamine hydrochloride, C13H18 Powder Diffr.201732, 193-195. DOI:10.1017/S0885715617000586

  2. Bajzíková, K.; Svoboda, J.; Novotná, V.; Pociecha, D.; Gorecka E.: Bent-core mesogens with an aromatic unit at the terminal position. New J. Chem.201741, 4672-4679 DOI: 1039/C6NJ03908A

  3. Žurek, J.; Svobodová, E.; Šturala, J.; Dvořáková, H.;Svoboda, J.; Cibulka, R.: Chiral ethylene-bridged flavinium salts: The stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties. Tetrahedron Asymmetry 2017, 28, 1780-1791. DOI:1016/j.tetasy.2017.10.029

  4. Dobrovolny, K.; Ulbrich, P.; Svecova, M.; Rimpelova, S.; Malincik, J.; Kohout, M.; Svoboda, J.; Bartunek, V.: Copper nanoparticles in glycerol-​polyvinyl alcohol matrix: In situ preparation, stabilization and antimicrobial aktivity. Alloy. Compd.2017, 697, 147-155 DOI:10.1016/j.jallcom.2016.12.144

  5. Kolderova, N.; Nevesely, T.; Sturala, J.; Kuchar, M.; Holakovsky, R.; Kohout, M.:
    Enantioseparation of chiral sulfoxides on amylose-​based columns: comparison of normal phase liquid chromatography and supercritical fluid chromatography Chromatographia 201780, 547-557 DOI: 10.1007/s10337-016-3234-6

  6. Kohout, M.; Alaasar, M.; Poryvai, A.; Novotna, V.; Poppe, S.; Tschierske, C.; Svoboda, J.: Photosensitive bent-​core liquid crystals based on methyl substituted 3-​hydroxybenzoic acid
    RSC Adv.20177, 35805-35813 DOI:10.1039/C7RA05632J

  7. Wolrab, D.; Fruehauf, P.; Gerner, C.; Kohout, M.;Lindner, W.: Consequences of transition from liquid chromatography to supercritical fluid chromatography on the overal performance of a chiral zwitterionic ion-​exchanger. J. Chromatogr. A 20171517, 165-175 DOI:10.1016/j.chroma.2017.08.022

  8. Pallova, L.;Kozmik, V.; Kohout, M.; Svoboda, J.; Novotna, V.; Pociecha, D.: Bent-​core liquid crystals with a 2-​substituted 3-​hydroxybenzoic acid central core. Cryst. 201744, 1306-1315 DOI: 10.1080/02678292.2016.1276981

  9. Tlusty, M.; Slavik, P.; Kohout, M.; Eigner, V.; Lhotak, P.: Inherently Chiral Upper-Rim-Bridged Calix[4]arenes Possessing a Seven Membered Ring
    Org. Lett. 201719, 2933-2936 DOI:10.1021/acs.orglett.7b01170

  10. Miksatko, J.; Eigner, V.; Kohout, M.; Lhotak, P.: Regio-/stereoselective Formation of Monosulfoxides from Thiacalix[4]arenes in All Possible Conformations
    Tetrahedron Letters 201758, 1687–1691 DOI:10.1016/j.tetlet.2017.03.043

  11. Horčic, M.; Kohout, M.; Svoboda, J.; Novotna, V.; Pociecha, D.; Gorecka, E.: Core-to-core Dimers Forming Switchable Mesophase
    Chem.  Commun. 201753, 2721-2724 DOI:10.1039/C6CC09983A

  12. März, M.; Chudoba, J.; Kohout, M.; Cibulka, R.: Photocatalytic Esterification under Mitsunobu Reaction Conditions Mediated by Flavin and Visible Light
    Org. Biomol. Chem. 2017, 15, 1970-1975 DOI:10.1039/C6OB02770A

Publications 2016

  1. Bajzikova, K.; Kohout, M.; Tarabek, J.; Svoboda, J.; Novotna, V.; Vejpravova, J.; Pociecha, D.; Gorecka, E.: All-organic liquid crystalline radicals with a spin unit in the outer position of a bent-core systém. J. Mater. Chem. C20164, 11540-11547.  DOI:10.1039/C6TC04346A

  2. Tůma, J.; Kohout, M.; Svoboda, J.; Novotná, V.; Pociecha, D.: Bent-core liquid crystals based on 6-substituted 3-hydroxybenzoic acid: the role of substitution and linkage group orientation on mesomorphic properties. Liq. Cryst.201643, 1889-1900.  DOI:10.1080/02678292.2016.1230789

  3. Kohout, M.; Vandenbussche, J.; Roller, A.; Tůma, J.; Boqaerts, J.; Bultinck, P.; Herrebout, W.; Lindner, W.: Absolute configuration of the antimalarial erythro-mefloquine - vibrational dichroism and X-ray diffraction studies of mefloquine and its thiourea derivative. RSC Advances20166, 81461-81465. DOI:1039/C6RA19367F 

  4. Kohout, M.; Bubnov, A.; Šťurala, J.; Novotná, V.; Svoboda, J.: Effect on alkyl chain length in the terminal ester group on mesomorphic properties of new chiral lactic acid derivatives. Cryst.201643, 1472-1485. DOI:10.1080/02678292.2016.1185170

  5. Grecsó, N.; Kohout, M.; Carotti, A.; Sardella, R.; Natalini, B.; Fülöp, F.; Lindner, W.; Péter, A.; Ilisz, I.: Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds. Pharm. Biomed. Anal.2016124, 164-173. DOI:10.1016/j.jpba.2016.02.043

  6. Wolrab, D.; Frühauf, P.; Moulisova, A.; Kuchar, M.; Gerner, C.; Lindner, W.; Kohout, M.: Chiral separation of new designer drugs (Cathinones) on chiral ion-exchange type stationary phases. Pharm. Biomed. Anal.2016120, 306-315. DOI:10.1016/j.jpba.2015.12.023

  7. Tůma, J.; Kohout, M.; Svoboda, J.; Novotná, V.; Pociecha, D.: Bent-shaped liquid crystals based on 4-substituted 3-hydroxybenzoic acid central core - Part II.  Cryst. 201643, 547-563 DOI: 10.1080/02678292.2015.1125535

  8. Slavik, P.; Kohout, M.; Böhm, S.; Eigner, V.; Lhotak, P.: Synthesis of Inherently Chiral Calixarenes via Direct Mercuration of the Partial Cone Conformation. Chem. Comm.  201652, 2366-2360 DOI:10.1039/C5CC09388K

Publications 2015

  1. Trišović, N.; Antanasijević, J.; Tóth-Katona, T.; Kohout, M.; Salamonczyk, M.; Sprunt, S.; Jákli, A.; Fodor-Csorba, K.: Azo-containing asymmetric bent-core liquid crystals with modulated smectic phase RSC Adv. 2015, 5, 64886-64891. DOI: 10.1039/c5ra09764a

  2. Kohout, M.; Bielec, B.; Steindl, P.; Trettenhahn, G.; Lindner, W.: Mechanistic aspects of the direct C-acylation of cyclic 1,3-diones with various unactivated carboxylic acids Tetrahedron 2015, 71, 2698-2707. DOI: tet.2015.03.037

  3. von Koschitzky, I.; Gerhardt, H.; Lämmerhofer, M.; Kohout, M.; Gehringer, M.; Laufer, S.; Pink, M.; Schmitz-Spanke, S.; Strube, C.; Kaiser, A.: New insights into novel inhibitors against deoxyhypusine hydrolase from plasmodium falciparum: compounds with an iron chelating potential Amino Acids 2015, 47, 1155-1166. DOI: 1007/s00726-015-1943-z

  4. Kohout, M.; Kozmík, V.; Slabochová, M.; Tůma, J.; Svoboda, J.; Novotná, V.; Pociecha, D.: Bent-shaped liquid crystals based on 4-substituted 3-hydroxybenzoic acid central core Cryst. 2015, 42, 87-103. DOI: 10.1080/02678292.2014.965232

  5. Kozmík, V.; Poznik, M.; Svoboda, J.; Frere, P.:
    Dithieno[3,2-b:2',3'-d]furan as a new building block for fused conjugated systems
    Tetrahedron Lett.201556, 6251-6253. DOI:10.1016/j.tetlet.2015.09.107
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GAČR

 ◳ Experientia
 ◳UCT Prague







Who we are and what we are interested in?

Start-up group: Dynamic systems chemistry for adaptive organic materials (since January 2021)

Molecules are constantly moving and interacting with other molecules and their environment. If these interactions involve bond formation and its breakage, sharing reactants/products, a whole reaction network is created. The boundaries between the phases are an important phenomenon, e.g. for membranes, for heterogeneous catalyst, for living cells. While reaction networks deal with covalent bonding between atoms, an interface is responsible for surface adsorption and self-assembly of whole molecular systems. We aim to investigate complex reaction networks coupling covalent and non-covalent interactions at surfaces and phase interfaces as a tremendously exciting direction of research.

We give high importance to international mobility because we see it as a key tool for the growth of both students and researchers. We are proud of the diversity of our group and we strongly support international cooperation programs (e.g. Erasmus+, internships, etc.).

If you are a motivated student endorsing organic synthesis as a tool to discover functionality of molecular assemblies that goes beyond the state-of-the-art, join us!

Group_2022_03

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Group leader

Kovaříček Petr, Ing., Ph.D.
Building A, room 266
+ 420 220 44 4165
Petr.Kovaricek@vscht.cz 

Post docs

Guerra Valentino L. P., Ph.D.
Valentino.Guerra@vscht.cz

Varghese Beena, Ph.D.
  Beena.Varghese@vscht.cz

Harry Robson, Ph.D.
  Harry.Robson@vscht.cz

PhD students

Strnadová Tereza, Ing.
Tereza.Strnadova@vscht.cz

Heleveria Anna, MSc.
Anna.Heleveria@vscht.cz

Šetek Martin, Ing.
Martin.Setek@vscht.cz

Heinz Killiann, MSc.
Killiann.Heinz@vscht.cz

Office

Building ZB3, room 207
+ 420 220 44 2040

Lab

Building A, room 262
+ 420 220 44 4276

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Research:

Our research axes are:

Dynamic reaction networks

Synthesis of individual components of a library that upon mixing forms all possible combinations. All reactions, however, are coupled by sharing their reactants/product thus forming a reaction network. Each particular product features distinct properties that can be addressed by external stimuli, making it adaptive. And adaptation is the key prerequisite for evolution.

 Dynamic reaction networks


Self-assembly at surfaces and interfaces

Self-assembly at surfaces and interfaces

Introducing a phase interface, e.g. a solid surface, inherently imposes a bias on the system. Due to differences in surface adsorption enthalpies among the species present, the composition of the layer adsorbed on the surface will be complementary to that in the other phase. A phase interface represents a significant energy step for physisorbing molecules comparable to the activation energy of a reversible bond formation/exchange barrier. We aim to understand how the surface instruct self-organization of species in its proximity and how molecules ‘feel’ the presence of the surface.










Heterogeneous photo-organo-catalysis

Molecules and the surface that they are assembled on exchange energy and electrons so that excited states can travel from the substrate to the molecule (or vice versa). Molecular excited state can adopt many roles such as a reagent or a catalyst. Organic molecules in their vast structural variations can recognize each other and therefore can be potent organocatalysts. We want to ‘shed the light’ on organocatalysis at surfaces… literally!

 Heterogeneous photo-organo-catalysis


Surfaces for biochemical and biomedical applications

Surfaces for biochemical and biomedical applications

Every cell is defined by its boundary with the world around – cell membrane – which is an amazingly complex ‘surface’, an example of a triple liquid phase interface. We are interested in surfaces which interact with biomolecules, cellular structures or even whole cells and can be used as sensors of these biomolecules or for cellular biology studies of the structures (e.g. membranes). By studying the phase boundary we break down inter-disciplinary boundaries!

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People:


Group leader:

Kovaricek


Dr. Petr Kovaříček

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Assistant professor

Ph.D. 2014, University of Strasbourg, France


Technician:

Michaela Kadlecová


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Laboratory technician

Researchers:

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Dr. Valentino L. P. Guerra


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Post-Doctoral researcher

Ph.D. 2017, University of Salento, Italy

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Dr. Beena Varghese

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Post-Doctoral researcher

Ph.D. 2015, Sultan Qaboos University, Oman

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Dr. Harry Robson

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Post-Doctoral researcher

Ph.D. 2021, Sheffield University, UK

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Dr. Rimeh Ismail

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Post-Doctoral researcher

Ph.D. 2020, University of Tunis El Manar, Tunisia

PhD students:

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MSc. Tereza Strnadová


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Ph.D. student (D1)

MSc. 2018, Czech Technical University, Czech Republic

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MSc. Anna Heleveria

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Ph.D. student (D3)

MSc. 2019, Kharkiv National University, Ukraine

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MSc. Martin Šetek

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Ph.D. student (D1)

MSc. 2022, University of Chemistry and Technology Prague, Czech Republic

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MSc. Killiann Heinz


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Ph.D. student (D1)

MSc. 2022, Université de Rennes, France

Undergraduate students:

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Karolína Křížová

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Master student (M2)

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Phuong Hoang

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Master student (M2)

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Margarita Faizulina

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Bachelor student (M1)

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Anna Nožičková

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Master student (M1)

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Marián Moravčík

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Bachelor student (B2)

Chiara Ciotta

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Erasmus+ internship from Italy 2022

 

Bengisu Akin

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Erasmus+ internship from Turkey 2022

Arda Küçük

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Erasmus+ internship from Turkey 2023

Alumni:

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Damien Bermon

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Erasmus+ traineeship from France 2022

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Natalia Montero Sánchez-Campíns

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Erasmus+ internship from Spain 2021

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Pia Kappeler

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Internship from Switzerland 2021

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Daria Artemieva

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Laboratory technician
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Lab equipment:

Triple channel DC power supply

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Digital multimeter

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Source measure unit

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HPLC

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Contact angle goniometer

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Ossila - Spin Coater


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PalmSens4 - Potentiostat / Galvanostat / Impedance Analyzer

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Ocean Insight – PX-2 Pulsed Xenon Lamp

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Nanosurf – NaioAFM

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Ocean Insight – USB650UV Miniature Spectrometer

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Quantum Design - Tunable monochromatic light source

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Group of quantum chemistry and mechanochemistry

!! HIRING !! We are hiring PhD student for our grant project.

 

Research topic:
- Application of quantum mechanical methods for prediction of properties of designed molecules
- Calculation of spectroscopic properties
- Design and optimization of molecular structures for mechanochemical applications
- Synthesis of mechanically sensitive compounds
- Development of ab-initio methods, multirefence configuration interaction and open-shell coupled cluster

 exc (šířka 450px)

We are looking for:
- Adepts of organic chemistry
- Fans of computational chemistry (and programmers interested in parallel methods)
 … with good grades and interests in lab work (starting at first year)

 

We offer:
- Working atmosphere and support for writing bachelor and master theses
- Interesting projects
- In-depth experience of quantum chemical methods and practical skills through research participation
- International collaboration including stays abroad
- Presentation of results on international meetings

trhani (šířka 450px)

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WELCOME TO THE GROUP OF ORGANOFLUORINE CHEMISTRY

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WE ARE LOOKING FOR Bc., M.Sc. and Ph.D. STUDENTS

We offer:

  • interesting projects focused mainly on fluorinated organic compounds
  • practical knowledge of organic synthesis
  • international collaboration with the possibility of an internship abroad
  • presentation of results at national and international conferences
  • introduction to computational and visualization methods for theoretical studies
  • friendly atmosphere

 
Our latest achievements:

Three of our students were successfull at Student’s Scientific Conference 20230 organized by UCT Prague. Vít Jeníček placed first, Adam Hroch placed second  and Kryštof Malyh placed second in their sessions.

Two of our students were successfull at Student’s Scientific Conference 2022 organized by UCT Prague. Michal Trojan placed first and Adam Hroch placed third in their sessions.


Our latest publications:

 

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Financial support


Current grant projects:

„Advanced reagents for (asymmetric) nucleophilic fluorination.“ (GA CR, 2021-2023)

Cooperation:

Grant project EXPRO: „Nanocrystallography of molecular crystals“ (GA CR, 2021-2025)

European Regional development Fund-Project "Organic redox couple based batteries for energetics of traditional and renewable resources (ORGBAT)" No.CZ.02.1.01/0.0/0.0/16_025/0007445.

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Group members:

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Employees

Prof. Ing. Jaroslav Kvíčala, CSc.

 

Ing. Markéta Rybáčková, Ph.D.

 

Helena Štenglová



Ph.D. students

 

Ing. Pavlína Dundálková

Ing. Kateřina Kučnirová

Bc. Šárka Bouzková

Students

Bc. Vít Jeníček 

Bc. Adam Hroch

Bc. Šárka Polívková

Bc. Sámer Melhem


Bc. Ondřej Ježowicz

Bc. Kryštof Malý

Jan Mikuláštík

Nadiia Silina

Jakub Krebs


Martina Wágnerová

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Current topics studied in our group:

  • Chiral NHC ligands and fluorination reagents
  • Ring opening metathesis of strained fluorocycloalkenes
  • Computational studies of reaction mechanisms
  • Chiral fluorous recyclable ruthenium and palladium catalysts

We have developed polyfluoroalkylated Hoveyda-Grubbs second-generation precatalyst analogues and PEPPSI catalyst analogues, that can be recycled using medium fluorous separation methods. This approach utilizes hydrofluoroethers such as HFE 7100 or HFE 7500, which are environmentally acceptable in comparison to perfluorinated solvents.


  • Ring-closing metathesis of prochiral oxaendiynes

Prochiral oxaendiynes undergo chemoselective ring-closing metathesis affording 2H-pyran derivatives, which can be further transformed into tricyclic compounds via chemo- and stereoselective Diels-Alder reaction.



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Selected publications

2020

Kolarikova, V.; Rybackova, M.; Svoboda, M.; Kvicala, J.:
Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans
Beilstein J. Org. Chem.  2020, 16, 2757–2768 DOI:10.3762/bjoc.16.226

Simunek, O.; Rybackova, M.; Svoboda, M.; Kvicala, J.:
Synthesis, catalytic activity and medium fluorous recycle of fluorous analogues of PEPPSI catalysts
J. Fluorine Chem. 2020, 236, 109588 DOI:10.1016/j.jfluchem.2020.109588

2018

Mundil, R.; Sokolohorskyj, A.; Hosek, J.; Cvacka, J.; Cisarova, I.; Kvicala, J.; Merna, J.:
Nickel and palladium complexes with fluorinated alkyl substituted α-diimine ligands for living/controlled olefin polymerization
Polym. Chem. 2018, 9, 1234-1248 DOI: 10.1039/C8PY00201K

Hosek, J.; Simunek, O.; Lipovska, P.; Kolarikova, V.; Kucnirova, K.; Edr, A.; Stepankova, N.; Rybackova, M.; Cvacka, J.; Kvicala, J.:
Medium Fluorous Separation Using Hydrofluoroether and Weakly Polar Solvents for Environmentally Friendly Recycling of Catalysts
ACS Sustainable Chem. Eng.  2018, 6, 7026-7034 DOI:10.1021/acssuschemeng.8b00865

Kucnirova, K.; Simunek, O.; Rybackova, M.; Kvicala, J.:
Structural Assignment of Fluorocyclobutenes by 19F NMR Spectroscopy – Comparison of Calculated 19F NMR Shielding Constants with Experimental 19F NMR Shifts
Eur. J. Org. Chem. 2018, 3867-3874 DOI:10.1002/ejoc.201800482

2016

Lipovska, P.; Rathouska, L.; Simunek, O.; Hosek, J.; Kolarikova, V.; Rybackova, M.; Cvacka, J.; Svoboda, M.; Kvicala, J.:
Synthesis and catalytic activity of ruthenium complexes modified with chiral racemic per- and polyfluorooxaalkanoates
J. Fluorine Chem. 2016, 191, 14-22 DOI:10.1016/j.jfluchem.2016.09.005

Dolenský, B.; Kvíčala, J.; Paleta, O.  Methyl fluoroalkanoate as methyl-​transferring reagent. Unexpected participation of BAl2 (SN2) mechanism in the reaction of methyl 2,​3,​3,​3-​tetrafluoro-​2-​methoxypropanoate with amines. J. Fluorine Chem. 2016, 185, 31-35. DOI:10.1016/j.jfluchem.2016.02.012



2015

Kolaříková, V.; Šimůnek, O.; Rybáčková, M.; Cvačka, J.; Březinová, A.; Kvíčala, J. Transition Metal Complexes Bearing NHC Ligands with Secondary Polyfluoroalkyl Groups. J. Chem. Soc., Dalton Trans., 201544, 19663-19673. DOI:10.1039/C5DT02258D 

 

Rybáčková, M.; Hošek, J.; Šimůnek, O.; Kolaříková, V.; Kvíčala, J. Computational study of productive and non-productive cycles in fluoroalkene metathesis. Beilstein J. Org. Chem. 201511, 2150–2157. DOI:10.3762/bjoc.11.232

 

 Hošek, J.; Rybáčková, M.; Čejka, J.; Cvačka, J.; Kvíčala, J.:  Synthesis of heavy Fluorous Ruthenium Metathesis catalysts using the stereoselective addition of polyfluoroalkyllithium to sterically hindered diimines. Organometallics 2015, 34(13), 3327-3334. DOI:10.1021/acs.organomet.5b00325

 

2014

Babuněk, M.; Šimůnek, O.; Hošek, J.; Rybáčková, M.; Cvačka, J.; Březinová, A.; Kvíčala, J. Heavy fluorous phosphine-free ruthenium catalysts for alkene metathesis. J. Fluorine Chem., 2014, 161, 66-75. DOI:10.1016/j.jfluchem.2014.03.003

 

2013

 

Kvíčala, J.; Schindler, M.; Kelbichová, V.; Babuněk, M; Rybáčková, M.; Kvíčalová, M.; Cvačka, J.; Březinová, A.: Experimental and theoretical study of Hoveyda-Grubbs catalysts modified by perfluorohexyl ponytail in the alkoxybenzylidene ligand. J. Fluorine Chem., 2013, 153, 12-25. DOI:10.1016/j.jfluchem.2013.06.001

 

2012

 

Skalický, M.; Skalická, V.; Paterová, J.; Rybáčková, M.; Kvíčalová, M.; Cvačka, J.; Březinová, A.; Kvíčala, J.: Ag Complexes of NHC ligands Bering Polyfluoroalkyl and/or Polyfluoropolyalkoxy Ponytails. Why Are Polyethers More Fluorous Than Alkyls. Organometallics, 2012, 31, 1524-1532. DOI:10.1021/om201062c

 

2011

 

Skalická, V.; Rybáčková, M.; Skalický, M.; Kvíčalová, M.; Cvačka, J.; Březinová, A.; Čejka, J.; Kvíčala, J.: Polyfluoroalkylated Tripyrazolylmethane Ligands: Synthesis and Complexes. J. Fluorine Chem. 2011, 132, 434-440. DOI:10.1016/j.jfluchem.2011.04.010

 

2010

 

Paterová, J.; Skalický, M.; Rybáčková, M.; Kvíčalová, M.; Cvačka, J.; Kvíčala, J.: Synthesis of 2-(perfluoroalkyl)ethyl potassium sulfates based on perfluorinated Grignard reagents. J. Fluorine Chem. 2010, 131, 1338-1343. DOI:10.1016/j.jfluchem.2010.09.003

Kvíčala, J.; Beneš, M.; Paleta, O.; Král, V.: Regiospecific nucleophilic substitution in 2,3,4,5,6-pentafluorobiphenyl as model compound for supramolecular systems. Theoretical study of transition states and energy profiles, evidence for tetrahedral SN2 mechanism. J. Fluorine Chem. 2010, 131, 1327-1337. DOI:10.1016/j.jfluchem.2010.09.003

 

2009

 

Skalický, M.; Rybáčková, M.; Kysilka, O.; Kvíčalová, M.; Cvačka, J.; Čejka, J.; Kvíčala, J.: Synthesis of bis(polyfluoroalkylated)imidazolium salts as key intermediates for fluorous NHC ligands. J. Fluorine Chem. 2009, 130, 966-973. DOI:10.1016/j.jfluchem.2009.07.015

Kysilka, O.; Rybáčková, M.; Skalický, M.; Kvíčalová, M.; Cvačka, J.; Kvíčala, J.: Fluorous imidazolium room-temperature ionic liquids based on HFPO trimer. J. Fluorine Chem. 2009, 130, 629-639. DOI:10.1016/j.jfluchem.2009.04.006

 

2008

 

Kysilka, O.; Rybáčková, M.; Skalický, M.; Kvíčalová, M.; Cvačka, J.; Kvíčala, J.: HFPO trimer-based alkyl triflate, a novel building block for fluorous chemistry. Preparation, reactions and 19F gCOSY analysis. Collect. Czech. Chem. Commun. 2008, 73(12), 1799-1813. DOI:10.1135/cccc20081799

 

2007

 

Pomeisl, K.; Čejka, J.; Kvíčala, J.; Paleta, O.: Synthesis of 3-fluorofuran-2(5H)-ones based on Z/E photoisomerisation and cyclisation of 2-fluoro-4-hydroxybut-2-enoates. Eur. J. Org. Chem. 2007, 5917-5925.

Hajduch, J.; Paleta, O.; Kvíčala, J.; Haufe, G.: Fluorinated furan-2(5H)-ones: reactivity and stereoselectivity in Diels-Alder reactions. Eur. J. Org. Chem. 2007, 5101-5111.

Pomeisl, K.; Kvíčala, J.; Paleta, O.; Klásek, A; Kafka, S.; Kubelka, V.; Havlíček, J.; Čejka, J.: Limitations of the Wittig-Horner-type annulation of fluorobutenolide moiety to 3-hydroxyquinoline-2,4(2H,3H)-diones. Novel modifications of the Perkow reaction including fluorinated acyloxy leaving groups. Tetrahedron 2007, 63, 10549-10561.

Červenková Šťastná L.; Auerová, K.; Kvíčala, J.; Čermák, J.: Fluorophilic properties of (perfluorooctyl)ethyldimethylsilyl substituted and tetramethyl(perfluoroalkyl) substituted cyclopentadienes and their Ti(IV), Rh(III), and Rh(I) complexes. J. Organomet. Chem. 2007, 692, 1974-1982.

 

2006

 

Pomeisl, K.; Kvíčala, J.; Paleta, O.: Convenient Synthesis of 3-Fluoro-4,5-diphenylfuran-2(5H)-one from Benzoin Ethers. Novel and Efficient Z-E Isomerisation and Cyclisation of 2-Fluoroalkenoate Precursors, Substitution of Vinylic Fluorine. J. Fluorine Chem. 2006, 127, 1390-1397.

Kvíčala, J.; Baszczyňski, O.; Krupková, A.; Stránská, D.: Hydroboration of 1,1’-Bi(cyclopent-1-ene) and 3,3’-Biindene: Experimental and Theoretical Study. Collect. Czech Chem. Commun. 2006, 71, 1611-1626.

 

2005

 

Kvíčala, J.; Štambaský, J.; Skalický, M.; Paleta, O.: Preparation of Fluorohalomethyl-magnesium Halides Using Highly Active Magnesium Metal and Their Reactions. J. Fluorine Chem. 2005, 126, 1390-1395.

Dolenský, B.; Kvíčala, J.; Paleta, O.: Methyl 3,3,3-Trifluoropyruvate Hemiaminals: Stability and Transaminations. J. Fluorine Chem. 2005, 126, 745-751.

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Supramolecular Chemistry Group

at DOC UCT Prague

Anyone who might be interested in calixarene and/or supramolecular chemistry, please contact Prof. Pavel Lhoták via e-mail: lhotakp@vscht.cz or tel.: +420 220 445 055.

Chem. Commun. 2014, 50, 6749-6751, http://dx.doi.org/10.1039/C4CC02274B

New J. Chem. 2016,  40, 1104-1110, http://dx.doi.org/10.1039/C5NJ02427G

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 ◳ 2022 group photo

Group Leader:

Prof. Pavel Lhoták

 

 

   

Associate Professor: 

 Assoc. Prof. Jan Budka

 

 

   

Assistent Professor:

 Dr. Ondrej Kundrat

 

 

   

PhD Students: 

   

 

 MSc. Tomáš Landovský (D7+)  
   MSc. Daniel Kortus (D5)  
   MSc. Anastasia Surina (05)  
   MSc.  Kamil Mamleev (D4)  
 MSc.  Michal Churý (D1)

Students:  

   
 Hynek Varga (M2)
 Karolína Vatrová (M2)
 Jaroslav Nedbalý (B3)
   Monika Nešněrová (B3)  
 Tadeáš Petrů (B2)
 Lukáš Smejkal (B2)
 Libor Kuchař (B2)
 Karla Hovorková (B2)

Technician:

 MSc. Ivana Bocková

 
     

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In the last years, we have been focusing on inherently chiral derivatives which can be obtained via relatively simple reactions in the meta-position of a (thia)caliarene skeleton (see publications); some examples of last results:
 

Intramolecularly Bridged Calix[4]arenes with Pronounced Complexation Ability toward Neutral Compounds

Slavik, P.; Eigner, V.; Lhotak, P.
Org. Lett. 2015, 17, 2788-2791
 DOI:10.1021/acs.orglett.5b01200 


Abstract Image 

Abstract: Regioselective derivatization via an organomercury intermediate allowed for the introduction of carboxylic acid functionality into the meta position of the calix[4]arene skeleton. Intramolecular Friedel–Crafts cyclization led to a novel type of calixarene containing a ketone bridging moiety. Subsequent attack of the ketone by organometallic compounds occurred selectively from outside providing tertiary alcohols with the OH group oriented inside the cavity. These compounds can complex neutral molecules both in the solid state (X-ray) and in solution (NMR) using the cooperative effect of hydrogen bonding (OH) and CH−π interactions from within the cavity.

 

Shaping of Calix[4]arenes via Double Bridging of the Upper Rim

Slavik, P.; Eigner, V.; Lhotak, P.
Cryst. Eng. Comm. 2016, 18, 4964-4970
DOI:10.1039/C6CE00314A

 

Graphical abstract: Shaping of calix[4]arenes via double bridging of the upper rim 

 

Abstract: Direct double meta-mercuration can be used for subsequent bridging of a calix[4]arene skeleton via the installation of ketone moieties. This unprecedented substitution pattern in calixarene chemistry possesses a heavily distorted and rigid cavity capable of interactions with selected molecular guests as documented by binding of a CH2Cl2 molecule held in place by an intricate net of 10 specific (halogen bonding and hydrogen bonding) interactions from two neighbouring calixarene molecules

 


Calix[4]arene Containing a Ureido Functionality on the Lower Rim as Highly Efficient Receptors for Anion Recognition

Klejch, T.; Slavicek, J.; Hudecek, O.; Eigner, V.; Gutierrez, N. A.; Curinova, P.; Lhotak, P.

New J. Chem. 2016, 40, 7935-7942
 DOI:10.1039/c6nj01271j


Graphical abstract: Calix[4]arenes containing a ureido functionality on the lower rim as highly efficient receptors for anion recognition

 

Abstract: The introduction of nosyl moieties onto the lower rim of the calix[4]arene skeleton led to the formation of compounds immobilised in cone conformations. Subsequent reduction of the nitro group and reaction with aryl isocyanates enabled the construction of new calixarene-based ligands for anion recognition. As proven by NMR and UV/vis titration experiments, diaryl urea moieties with electron-withdrawing substituents on both sides represent very efficient tools for the complexation of selected anions (AcO, BzO, H2PO4) even in highly competitive solvents such as DMSO-d6.

 

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2022:

 

Liška, A.; Řezanková, M.; Klíma, J.; Urban, J.; Budka, J.; Ludvík, J.:
Electrochemical, EPR, and quantum chemical study of reductive cleavage of cone-Calix[4]arene nosylates – New electrosynthetic approach
Electrochem. Sci. Adv.
2022, e2100221, DOI: org/10.1002/elsa.202100221

 

 

2021:

 

 

 

Kortus, D.; Krizova, K.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

Synthesis of 2,8-dithiacalix[4]arene based on fragment condensation
Tetrahedron Lett. 2021, 69, 152924 DOI:10.1016/j.tetlet.2021.152924

Kortus, D.; Eigner, V.; Lhotak, P.:

Regio- and stereoselectivity of spirodienone formation in 2,14-dithiacalix[4]arene
New J. Chem. 2021, 45, 8563-8571 DOI:10.1039/d1nj01257f


Kortus, D.; Kundrat, O.; Cejka, J.; Dvorakova, H.; Lhotak, P.:

Chemistry of 2,14-Dithiacalix[4]arene: Searching for the Missing Fifth Conformer
J. Org. Chem. 2021 DOI:10.1021/acs.joc.1c01173

  

Curinova, P.; Winkler, M.; Krupkova, A.; Cisarova, I.; Budka, J.; Wun, C.N.; Blechta, V.; Maly, M.; Stastna-Cervenkova, L.; Sykora, J.; Strasak, T.:
Transport of Anions across the Dialytic Membrane Induced by Complexation toward Dendritic Receptors

ACS Omega 2021, 23, 15514-15522 DOI:10.1021/acsomega.1c02142

 

 

2020:

 

Horackova, T.; Budka, J.; Eigner, V.; Chung, W.-S.; Curinova, P.; Lhotak, P.:
Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation
Beilstein J. Org. Chem. 2020, 16, 2999-3007 DOI:10.3762/bjoc.16.249


Landovsky, T.; Eigner, V.; Babor, M.; Tichotova, M.; Dvorakova, H.; Lhotak, P.:

Regioselective SNAr reaction of the phenoxathiin-based thiacalixarene as a route to a novel macrocyclic skeleton
Chem. Commun. 2020, 56, 78-81 DOI:10.1039/c9cc08335a

Tlusty, M.; Dvorakova, H.; Cejka, J.; Kohout, M.; Lhotak, P.:

Regioselective formation of the quinazoline moiety on the upper rim of calix[4]arene as a route to inherently chiral systems
New J. Chem. 2020, 44, 6490-6500 DOI:10.1039/d0nj01035a

Kortus, D.; Kundrat, O.; Tlusty, M.; Cejka, J.; Dvorakova, H.; Lhotak, P.:
Inherent chirality through a simple dialkylation of 2,14-dithiacalix[4]arene
New J. Chem. 2020, 44, 14496-14504 DOI:10.1039/d0nj03468a

Tlusty, M.; Spalovska, D.; Kohout, M.; Eigner, V.; Lhotak, P.:
Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes
Chem. Commun. 2020, 56, 12773-12776 DOI:10.1039/d0cc05352j

 

Shishkanova, T.V.; Vatrskova, L.; Spalovska, D.; Kralik, F.; Curinova, P.; Winkler, M.; Budka, J.; Jurasek, B.; Kuchar, M.; Setnicka, V.:
Complexation of cathinones by 4-tert-butylcalix[4]arene tetra-acetate as a possible technique for forensic analysis
Forensic Toxicol. 2020, 38, 70-78 DOI:
10.1007/s11419-019-00489-8

 

 

 

2019:

 

 

 

Tlusty, M.; Spalovska, D.; Babor, M.; Lhotak, P.:

Synthesis of enantiomerically pure inherently chiral calix[4]​arenes using the meta-​substitution strategy
Tetrahedron Lett. 2019, 60, 260-263 DOI:10.1016/j.tetlet.2018.12.026

 

Slavik, P.; Krupicka, M.; Eigner, V.; Vrzal, L.; Dvorakova, H.; Lhotak, P.:

Rearrangement of meta-Bridged Calix[4]arenes Promoted by Internal Strain

J. Org. Chem. 2019, 84, 4229-4235, DOI:10.1021/acs.joc.9b00107


Kortus, D.; Miksatko, J.; Kundrat, O.;  Babor, M.; Eigner, V.; Dvorakova, H.; Lhotak, P.:

Chemistry of 2,14-Dithiacalix[4]arene: Alkylation and Conformational Behavior of Peralkylated Products

J. Org. Chem. 2019, 84, 11572-11580, DOI:10.1021/acs.joc.9b01493

 

Tlusty, M.; Eigner, V.; Babor, M.; Kohout, M.; Lhotak, P.:

Synthesis of Upper Rim-double-bridged Calix[4]​arenes bearing Seven Membered Rings and Related Compounds
RSC Advances 2019, 9, 22017-22030 DOI:10.1039/c9ra05075b

 

 

 

 

2018:

 

 

 

Landovsky, T.; Dvorakova, H.; Eigner, V.; Babor, M.; Krupicka, M.; Kohout, M.; Lhotak, P.:
Chemoselective Oxidation of Phenoxathiin-based Thiacalix[4]arene and the Stereoselective Alkylation of Products
New J. Chem. 201842, 20074-20086 DOI: 10.1039/C8NJ04690E

Slavik, P.; Eigner, V.; Lhotak, P.:

meta-​Bridged calix[4]​arenes with the methylene moiety possessing in​/out stereochemistry of substituents
New J. Chem. 201842, 16646-16652 DOI:10.1039/c8nj02577k


Landovsky, T.; Tichotova, M.; Vrzal, L.; Budka, J.; Eigner, V.; Dvorakova, H.; Lhotak, P.:

Structure elucidation of phenoxathiin-​based thiacalix[4]​arene conformations using NOE and RDC data
Tetrahedron 2018, 74, 902-907 DOI:10.1016/j.tet.2018.01.020


Slavik, P.; Dvorakova, H.; Krupicka, M.; Lhotak, P.:

Unexpected cleavage of upper rim-​bridged calix[4]​arenes leading to linear oligophenolic derivatives
Org. Biomol. Chem. 2018, 59, 838-843 DOI:10.1039/C7OB03101G

Slavik, P.; Lhotak, P.:

Unusual reactivity of upper-​rim bridged calix[4]​arenes - Friedel-​Crafts alkylation via cleavage of the macrocyclic skeleton
Tetrahedron 2018, 59, 1757-1759 DOI:10.1016/j.tetlet.2018.03.072

 

 

 

 

2017:

 
   

Bregier, F.; Hudecek, O.; Chaux, F.; Penouilh, M.; Chambron, J.; Lhotak, P.; Aubert, E.; Espinosa, E.:
Generation of Cryptophanes in Water by Disulfide Bridge Formation
Eur. J. Org. Chem. 2017, 3795-3811 DOI:10.1002/ejoc.201700537


Tlusty, M.; Slavik, P.; Kohout, M.; Eigner, V.; Lhotak, P.:
Inherently Chiral Upper-Rim-Bridged Calix[4]arenes Possessing a Seven Membered Ring
Org. Lett. 2017, 19, 2933-2936 DOI:10.1021/acs.orglett.7b01170

Slavik, P.; Eigner, V.; Bohm, S.; Lhotak, P.:
Mercuration of Calix[4]arene Immobilized in the 1,2- and 1,3-Alternate Conformations
Tetrahedron Letters 2017, 58, 1846-1850 DOI:10.1016/j.tetlet.2017.03.085

Miksatko, J.; Eigner, V.; Kohout, M.; Lhotak, P.:
Regio-/stereoselective Formation of Monosulfoxides from Thiacalix[4]arenes in All Possible Conformations
Tetrahedron Letters 2017, 58, 1687-1691 DOI:10.1016/j.tetlet.2017.03.043


Tlusty, M.; Slavik, P.; Dvorakova, H.; Eigner, V.; Lhotak, P.:
Synthesis and Study of Calix[4]arenes bearing Azo Moieties at the meta Position
Tetrahedron 2017, 73, 1230-1237 DOI:10.1016/j.tet.2017.01.025

Rezankova, M.; Budka, J.; Miksatko, J.; Eigner, V.; Cisarova, I.; Curinova, P.; Lhotak, P.:
Anion Receptors based on Intramolecularly Bridged Calix[4]arenes bearing Ureido Functions
Tetrahedron 2017, 73, 742–749 DOI:10.1016/j.tet.2016.12.054

 

 
   

2016:

 
   

Liska, A.; Lhotak, P.; Ludvik, J.:
Electrochemical Reduction and Intramolecular Electron  Communication of Nitro Substituted Thiacalix[4]arene
Electroanalysis 2016, 28, 2861-2865 DOI:10.1002/elan.201600342

 

Slavik, P.; Eigner, V.; Lhotak, P.:

A General Method for Obtaining Calixarene Derivatives in the 1,2-Alternate Conformation

Tetrahedron 2016, 72, 6348-6355 DOI:10.1016/j.tet.2016.08.028
 

Klejch, T.; Slavicek, J.; Hudecek, O.; Eigner, V.; Gutierrez, N. A.; Curinova, P.; Lhotak, P.:
Calix[4]arene Containing a Ureido Functionality on the Lower Rim as Highly Efficient Receptors for Anion Recognition
New J. Chem. 2016, 40, 7935-7942 DOI:10.1039/c6nj01271j

Miksatko, J.; Eigner, V.; Dvorakova, H.; Lhotak, P.:

Selective Oxidation of Thiacalix[4]arene (cone) to all Corresponding Sulfoxides

Tetrahedron Lett. 2016, 57, 3781–3784 DOI:10.1016/j.tetlet.2016.07.022

Slavik, P.; Eigner, V.; Lhotak, P.:
Shaping of Calix[4]arenes via Double Bridging of the Upper Rim

Cryst. Eng. Comm. 2016, 18, 4964-4970, DOI:10.1039/C6CE00314A

 

Botha, F.; Eigner, V.; Dvorakova, H.; Lhotak, P:

Arylation of Thiacalix[4]arenes using Organomercurial Intermediates

New J. Chem. 2016,  40, 1104-1110, DOI:10.1039/C5NJ02427G + cover picture


Slavik, P.; Kohout, M.; Bohm, S.; Eigner, V.; Lhotak, P.:

Synthesis of Inherently Chiral Calixarenes via Direct Mercuration of the Partial Cone Conformation

Chem. Comm. 2016, 52, 2366-2369, DOI:10.1039/C5CC09388K

 

Stejskal, F.; Curinova, P.; Lhotak, P.:
Unexpected Formation of Disulfide-based Biscalix[4]arenes
Tetrahedron 2016, 72, 760-766 DOI:10.1016/j.tet.2015.12.037

 

Kundrat, O.; Slavik, P.; Miksatko, J.:

Introducing an Amine Group to Calix[5]arene: Comparison of Several Methods

Supramol. Chem. 2016, 28, 450-454, DOI:10.1080/10610278.2015.1119275

   

   

 
   

2015:

 
   

Zajicova, M.; Eigner, V.; Budka, J.; Lhotak, P.:

Intramolecular Bridging of Calix[4]arene Dialdoximes

Tetrahedron Lett. 2015, 56, 5529–5532 DOI:10.1016/j.tetlet.2015.08.032

 

Vrzal, L.; Kratochvilova-Simanova, M.; Landovsky, T.; Polivkova, K.; Budka, J.; Dvorakova, H.; Lhotak, P.:

Application of RDC Enhanced NMR Spectroscopy in Structural Analysis of Thiacalix[4]arene Derivatives

Org. Biomol. Chem. 2015, 13, 9610-9618 DOI:10.1039/C5OB01424G

 

Stejskal, F.; Eigner, V.; Dvorakova, H.; Curinova, P.; Lhotak, P.:

Direct C-H Azidation of Calix[4]arene as a Novel Method to Access meta Substituted Derivatives

Tetrahedron Lett. 2015, 56, 5357-5361 DOI:10.1016/j.tetlet.2015.08.002

 

Slavik, P.; Eigner, V.; Lhotak, P.:
Intramolecularly Bridged Calix[4]arenes with Pronounced Complexation Ability toward Neutral Compounds
Org. Lett. 2015, 17, 2788-2791 DOI:10.1021/acs.orglett.5b01200

Liska, A.; Flidrova, K.; Lhotak, P.; Ludvik, J.:

Influence of Structure on Electrochemical Reduction of Isomeric Mono- and Di-, Nitro- or Nitrosocalix[4]arenes
Monatshefte fuer Chemie 2015, 146, 857-862 DOI:10.1007/s00706-015-1441-8

 

Hucko, M.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

2,14-Dithiacalix[4]arene and its Homooxa Analogues: Synthesis and Dynamic NMR Study of Conformational Behaviour

Chem. Comm. 2015, 51, 7051-7053 DOI:10.1039/C5CC00819K

 

Spendlikova, I.; John, J.; Cuba, V.; Jirasek, J.; Lhotak, P.:

Thiacalixarenes: Radiation Stability and Eu/Am Extraction in Synergistic Systems with COSANs

J. Radioanalyt. Nucl. Chem. 2015304, 257-262 DOI:10.1007/s10967-014-3694-9

 

Mackova, M.; Miksatko, J.; Budka, J.; Eigner, V.; Curinova, P.; Lhotak, P.:

Chiral Anion Recognition by a Ureido-Thiacalix[4]arene Ligand Immobilized in the 1,3-Alternate Conformation

New J. Chem. 2015, 39, 1382-1389 DOI:10.1039/C4NJ01956C

 

Flidrova, K.; Liska, A.; Ludvik, J.; Eigner, V.; Lhotak, P.:

Fullerene Recognition by 5-Nitro-11,17,23,29-tetramethylcalix[5]arene

Tetrahedron Lett. 2015, 56, 1535-1538 DOI:10.1016/j.tetlet.2015.02.016

 

Skacel, J.; Budka, J.; Eigner, V.; Lhotak, P.:

Regioselective Friedel-Crafts Acylation of Calix[4]arenes

Tetrahedron 2015, 71, 1959-1965 DOI:10.1016/j.tet.2015.02.021

 
   

2014:

 
   

Lukasek, J.; Böhm, S.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

Regioselective Halogenation of Thiacalix[4]​arenes in the Cone and 1,​3-​Alternate Conformations

Org. Lett. 2014, 16, 5100-5103 DOI: 10.1021/ol5024536

 

Slavik, P.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

Regioselective Alkylation of a Methylene Group via meta-bridging Calix[4]arenes

Chem. Commun. 2014, 50, 10112-10114 DOI:10.1039/C4CC04356A

 

Liska, A.; Rosenkranz, M.; Klima, J.; Dunsch, L.; Lhotak, P., Ludvik, J.:

Formation and Proof of Stable bi-, tri- and tetraradical Polyanions during the Electrochemical Reduction of cone-polynitrocalix[4]arenes. An ESR-UV-vis Spectroelectrochemical Study

Electrochimica Acta 2014, 140, 572-578 DOI:10.1016/j.electacta.2014.06.042

 

Botha, F.; Böhm, S.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

Mercuration of Thiacalix[4]​arenes in the Cone and 1,​3-​Alternate Conformations

Org. Biomol. Chem. 2014, 12, 5136-5143 DOI:10.1039/C4OB00799A

 

Vrzal, L.; Flidrova, K.; Tobrman, T.; Dvorakova, H.; Lhotak, P.:

Use of Residual Dipolar Couplings in Conformational Analysis of meta-disubstituted​ Calix[4]​arenes

Chem. Commun. 2014, 50, 6749-6751 DOI:10.1039/C4CC02274B

COVER PICTURE

 

Botha, F.; Budka, J.; Eigner, V.; Hudecek, O.; Vrzal, L.; Cisarova, I.; Lhotak, P.:

Recognition of Chiral Anions using Calix[4]arene-based Ureido Receptor in the 1,3-Alternate Conformation

Tetrahedron 2014, 70, 477-483 DOI:10.1016/j.tet.2013.11.030

 

Flidrova, K.; Bohm, S.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

Dimercuration of Calix[4]arenes: Novel Substitution Pattern in Calixarene Chemistry

Org. Lett. 2014, 16, 138-141 DOI:10.1021/ol403133b

 
 
 
 
 
 
 
 
 
 
 
 
 
    
 

2013:

 
   

Slavik, P.; Flidrova, K.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

Meta-​Arylation of Calixarenes using Organomercurial Chemistry

Org. Biomol. Chem. 2013, 11, 5528-5532 DOI:10.1039/c3ob41085d

 

Flidrova, K.; Slavik, P.; Eigner, V.; Dvorakova, H.; Lhotak, P.:

meta-​Bridged Calix[4]​arenes: A Straightforward Synthesis via Organomercurial Chemistry

Chem. Commun. 2013, 49, 6749-6751 DOI:10.1039/c3cc43284j

 

Holub, J.; Eigner, V.; Vrzal, L.; Dvorakova, H.; Lhotak, P.:

Calix[4]arenes with Intramolecularly Bridged meta Positions Prepared via Pd-catalysed Double C–H Activation

Chem. Commun. 2013,49, 2798-2800  DOI:10.1039/C3CC40655E

 

Mackova, M.; Himl, M.; Budka, J.; Pojarova, M.; Cisarova, I.; Eigner, V.; Curinova, P.; Dvorakova, H.; Lhotak, P.:

Self-assembly of 5,11,17,23-Tetranitro-25,26,27,28-tetramethoxythiacalix[4]arene with Neutral Molecules and its Use for Anion Recognition

Tetrahedron 2013, 69, 1397-1402 DOI:10.1016/j.tet.2012.10.101

 

Hudecek, O.; Budka, J.; Dvorakova, H.; Curinova, P.; Cisarova, I.; Lhotak, P.:

Anion Receptors based on Ureidocalix[4]arenes Immobilised in the Partial cone Conformation

New J. Chem. 2013, 37, 220-227 DOI:10.1039/c2nj40724h

 
 
 
 
 
 
 
 
 
    
 

2012:

 
   

Slavik, P.; Dudic, M.; Flidrova, K.; Sykora, J.; Cisarova, I.; Böhm, S.; Lhotak, P.:

Unprecedented meta-Substitution of Calixarenes: Direct Way to Inherently Chiral Derivatives

Org. Lett. 2012, 14, 3628-3631, DOI:10.1021/ol301420t

 

Kundrat, O.; Dvorakova, H.; Bohm, S.; Eigner, V.; Lhotak, P.:

S-Alkylation of Thiacalix[4]arenes: How the Regio- and Stereoselectivities Depend on the Starting Conformation

J. Org. Chem. 2012, 77, 2272-2278, DOI:1021/jo202571h

 

Hudecek, O.; Budka, J.; Eigner, V.; Lhotak, P.:

Regioselective ipso-Nitration of Calix[4]arenes

Tetrahedron 2012, 68, 4187-4193, DOI:10.1016/j.tet.2012.03.102

 

Flidrova, K.; Tkadlecova, M.; Lang, K.; Lhotak, P.:

Anion Recognition by Calix[4]arene–based p-Nitrophenyl Amides

Tetrahedron Lett. 2012, 53, 678-680, DOI:10.1016/j.tetlet.2011.11.127

 

Flidrova, K.; Tkadlecova, M.; Lang, K.; Lhotak, P.:

Anion Complexation by Calix[4]arene–TTF Conjugates

Dyes and Pigments 2012, 92, 668-673, DOI:10.1016/j.dyepig.2011.06.001

 
 
 
 
 
 
 
 
 

 

 
 
 

2011:

 

 

 

Kundrat, O.; Eigner, V.; Curinova, P.; Kroupa, J.; Lhotak, P.:

Anion-Binding by meta Ureido-Substituted Thiacalix[4]arenes

Tetrahedron 2011, 67, 8367-8372 DOI: 10.1016/j.tet.2011.08.062

 

Kundrat, O.; Eigner, V.; Dvorakova, H.; Lhotak, P.:

S-Alkylation of Thiacalixarenes: A Long-Neglected Possibility in the Calixarene Family

Org. Lett. 2011, 13, 4032-4035, DOI: 10.1021/ol201546y

 

Hudecek, O.; Curinova, P.; Budka, J.; Lhotak, P.:

Regioselective Upper Rim Substitution of Calix[4]arenes

Tetrahedron 2011, 67, 5213-5218, DOI: 10.1016/j.tet.2011.05.049

 

Mackova, M.; Himl, M.; Minarova, L.; Lang, J.; Lhotak, P.:

Regioselective Deuteration of 25,27-Dialkoxycalix[4]arenes

Tetrahedron Lett. 2011, 52, 2543-2546, DOI: 10.1016/j.tetlet.2011.03.030

 

Lhotak P., Kundrat O.: “Fullerene Receptors Based on Calixarene Derivatives“ in

Artificial Receptors for Chemical Sensors, Mirsky V., Yatsimirsky A. (Eds.), 2011, 249-272, Wiley-VCH Verlag, Weinheim, Germany, ISBN: 978-3-527-32357-9.

 
    
 

2010:

 
   

Kundrat, O.; Kroupa, J.; Bohm, S.; Budka, J.; Eigner, V.; Lhotak, P.:

Meta Nitration of Thiacalixarenes

J. Org. Chem. 2010, 75, 8372-8375, DOI: 10.1021/jo1013492

 

Snejdarkova, M.; Poturnayova, A.; Rybar, P.; Lhotak, P.; Himl, M.; Flidrova, K.; Hianik, T.:

High Sensitive Calixarene-Based Sensor for Detection of Dopamine by Electrochemical and Acoustic Methods

Bioelectrochemistry 2010, 80, 55-61, DOI: 10.1016/j.bioelechem.2010.03.006

 

Curinova, P.; Pojarova, M.; Budka, J.; Lang, K.; Stibor, I.; Lhotak, P.:

Binding of Neutral Molecules by p-Nitrophenylureido Substituted Calix[4]arenes

Tetrahedron 2010, 66, 8047-8050, DOI: 10.1016/j.tet.2010.08.006

 

Kriz, J.; Toman, P.;  Makrlik, E.; Budka, J.;  Shukla, R.; Rathore, R.:

Cooperative Interaction of Hydronium Ion with an Ethereally Fenced Hexaarylbenzene-Based Receptor: An NMR and Theoretical Study

J. Phys. Chem. A 2010114, 5327-5334; DOI: 10.1021/jp101080h

 

Budka, J.; Eigner, V.; Holakovsky, R.; Kovaricek, P.; Louzilova, T.:

25,26,27,28-Tetrapropoxycalix[4]arene-5,17-dicarbonitrile

Acta Crystallogr.E 2010, 66, O419-U3019; DOI: 10.1107/S1600536810002242

 

Van Rossom, W.; Kundrat, O.; Ngo, T. H.; Lhotak, P.; Dehaen, W.; Maes, W.:

An oxacalix[2]arene[2]pyrimidine-bis(Zn-porphyrin) tweezer as a selective receptor towards fullerene C70

Tetrahedron Lett. 2010, 51, 2423-2426; DOI: 10.1016/j.tetlet.2010.02.137

 

Kundrat, O.; Dvorakova, H.; Eigner, V.; Lhotak, P.:

Uncommon Regioselectivity in the Thiacalix[4]arene Series: Gross Formylation of the Cone Conformer

J. Org. Chem.2010, 75, 407-411; DOI: 10.1021/jo902240h

 

Bezouska, K.; Snajdrova, R.; Krenek, K.; Vancurova, M.; Kadek, A.; Adamek, D.; Lhotak, P.; Kavan, D.; Hofbauerova, K.; Man, P.; Bojarova, P.; Kren, V.:

Carboxylated calixarenes bind strongly to CD69 and protect CD69+ killer cells from suicidal cell death induced by tumor cell surface ligands

Bioorg.Med. Chem. 2010, 18, 1434-1440; DOI: 10.1016/j.bmc.2010.01.015

This article has been retracted at the request of the authors due to data fabrication and manipulation of exptl. material by the first author.

 

 

 
 
 

2009:

 
   

Kundrat, O.; Dvorakova, H.; Cisarova, I.; Pojarova, M.; Lhotak, P.:

Unusual Intramolecular Bridging Reaction in Thiacalix[4]arene Series

Org. Lett. 2009, 11, 4188-4191; DOI: 10.1021/ol901812m

 

Polívková, K., Šimánová, M., Budka, J., Cuřínová, P., Císařová, I., Lhoták, P.:

Unexpected behaviour of monospirothiacalix[4]arene under acidic conditions

Tetrahedron Lett, 2009, DOI: 10.1016/j.tetlet.2009.08.105

 

Kundrat, O.; Cisarova, I.; Bohm, S.; Pojarova, M.; Lhotak, P.:

Uncommon Regioselectivity in Thiacalix[4]arene Formylation

J. Org. Chem., 2009, 74, 4592-4596.

 

Kriz, J.; Dybal, J.; Makrlik, E.; Budka, J.; Vanura, P.:

Interaction of hydrated protons with trioctylphosphine oxide: NMR and theoretical study

J. Phys. Chem. A, 2009, 113, 5896-5905.

 

Makrlik, E.; Vanura, P.; Budka, J.:

On the protonation of dibenzo-18-crown-6

Monatsh. Chem., 2009, 140, 583-585.

 

Cuřínová, P.; Stibor, I.; Budka, J.; Sýkora, J.; Lang, K.; Lhoták, P.:

Anion Recognition by diureido-calix[4]arenes in the 1,3-alternate conformation

New J. Chem., 2009, 33, 612-619.

 

Makrlik, E.; Budka, J.; Vanura, P.; Selucký, P.:

Stability constants of some metal cation complexes of tetraphenyl p-tert-butylcalix[4]arene tetraketone in nitrobenzene saturated with water

Monatsh. Chem., 2009, 140, 157-160.

 
    
 

2008:

 
   

Kriz, J.; Dybal, J.; Makrlik, E.; Budka, J.:

Interaction of hydronium ion with dibenzo-18-crown-6: NMR, IR and theoretical study

J. Phys. Chem. A, 2008, 112, 10236-10243, 2009

 

Kriz, J.; Dybal, J.; Budka, J.; Makrlik, E.:

NMR and theoretical study of the kooperative interaction of hydrated proton with dibenzo-24-crown-8

Magn. Reson. Chem., 2008, 46, 1015-1024

 

Makrlik, E.; Budka, J.; Vanura, P.; Dybal, J.:

Solvent extraction of univalent cations into nitrobenzene using sodium dicarbollylcobaltate and tetraphenyl p-tert-butylcalix[4]arene tetraketone

Monatsh. Chem., 2008, 139, 1349-1351.

 

Dybal, J.; Makrlik, E.; Vanura, P.; Budka, J.:

DFT-calculated structure of protonated tetraphenyl p-tert-butylcalix[4]arene tetraketone

Monatsh. Chem., 2008, 139, 1353-1355.

 

Kriz, J.; Dybal, J.; Makrlik, E.; Budka, J.; Vanura, P.:

Protonation of tetrapropoxy-4-tert-butylcalix[4]arene: NMR study of interaction and probable structures of the product

Supramol. Chem., 2008, 20, 487-494.

 

Dybal, J.; Makrlik, E.; Vanura, P.; Budka, J.:

Protonation of 25,27-bis(1-octyloxy)-calix[4]arene-crown-6 in the 1,3-alternate conformation

Monatsh. Chem., 2008, 139, 1175-1178.

 

Kriz, J.; Dybal, J.; Makrlik, E.; Budka, J.:

Cooperative interaction of butylammonium ion with 1,3-alternate tetrapropoxycalix[4]arene: NMR and theoretical study

Magn. Reson. Chem., 2008, 46, 399-407.

 

Kriz, J.; Dybal, J.; Makrlik, E.; Budka, J.:

Cooperative interaction of H3O+ with 1,3-alternate tetrapropoxycalix[4]arene: NMR and theoretical study

Magn. Reson. Chem., 2008, 46, 235–243.

 

Kroupa J., Stibor I., Pojarová M., Tkadlecová M., Lhoták P.:

Anion receptors based on ureido-substituted thiacalix[4]arenes and calix[4]arenes

Tetrahedron 2008, 64, 10075-10079.

 

Kubát P., Lang K., Lhoták P., Janda P., Sýkora J., Matějíček P., Hofa M., Procházka K., Zelinger Z.:

Porphyrin/calixarene self-assemblies in aqueous solution

Photochem. Photobiol. A: Chemistry 2008, 198, 18-25.

 

Stibor I., Budka J., Michlová V., Tkadlecová M., Pojarová M., Curinová P., Lhoták P.:

The Systematic Approach to the New Ligands for Anion Recognition Based on Ureido-calix[4]arenes

New. J. Chem. 2008, 32, 1597-1607.

 

Lhoták P., Bílá A., Budka J., Pojarová M., Stibor I.:

Simple synthesis of calix[4]arenes in a 1,2-alternate conformation

Chem. Commun. 2008, 1662-1664.

 

Simánová M., Dvoráková H., Stibor I., Pojarová M., Lhoták P.:

Synthesis and conformational behaviour of lower-rim tetraacetylated thiacalix[4]arenes

Tetrahedron Lett. 2008, 49, 1026-1029.

 

Lang K., Prošková P., Kroupa J., Morávek J., Stibor I., Pojarová M., Lhoták P.:

The synthesis and complexation of novel azosubstituted calix[4]arenes and thiacalix[4]arenes

Dyes and Pigments 2008, 77, 646-652.

 
    
 

2007:

 
   

Krajewska A., Lhoták P., Radecka H.:

Potentiometric Responses of Ion-Selective Electrodes Doped with Diureidocalix[4]arene towards Un-dissociated Benzoic Acid

Sensors 2007, 7, 1655-1666.

 

Dvořáková H., Lang J., Vlach J., Sýkora J., Čajan M., Himl M., Pojarová M., Stibor I., Lhoták P.:

Partially O-Alkylated Thiacalix[4]arenes: Synthesis, Molecular and Crystal Structures, Conformational Behaviour

J. Org. Chem. 2007, 72, 7157-7166.

 

Kundrát O., Káš M., Tkadlecová M., Lang K., Cvačka J., Stibor I., Lhoták P.:

Thiacalix[4]arene-porphyrin conjugates with high selectivity towards fullerene C70

Tetrahedron Lett. 2007, 48, 6620-6623.

 

Křenek K., Kuldová M., Hulíková K., Stibor I., Lhoták P., Dudič M., Budka J., Pelantová H., Bezouška K., Fišerová A., Křen V.:

N-Acetyl-D-glucosamine substituted calix[4]arenes as stimulators of NK cell-mediated antitumor immune response

Carbohydr. Res. 2007, 342, 1781-1792.

 

Káš M., Lang K., Stibor I., Lhoták P.:

Novel fullerene receptors based on calixarene–porphyrin conjugates

Tetrahedron Lett. 2007, 48, 477-481.

 

Sýkora J., Himl M., Stibor I., Císařová I., Lhoták P.:

Unique Self-Assembly Patterns Based on Thiacalix[4]arene-Silver Interactions 

Tetrahedron 2007, 63, 2244-2248.

 

Budka J., Curinova P., Gu R., Lhotak P., Stibor I., Schraml J., Dehaen W.:

A Novel Calix[4]arene – Dipyrrole Conjugate Designed For Complexation Of Ion Pairs

Naturforsch. B  2007, 62B, 439-446.

 

 

 
 
 

2006:

 
   

Stastny V., Stibor I., Císařová I., Sýkora J., Pojarová M., Lhoták P.:

Synthesis of unique cage-like derivatives in a 1,3-alternate conformation

J. Org. Chem. 2006, 71, 5404-5406.

 

Lang J., Vágnerová K., Czernek J., Lhoták P.:

Flip-flop motion of circular hydrogen bond array in thiacalix[4]arene

Supramol. Chem. 2006, 18, 371-381.

 

Stastny V., Stibor I., König B.: Lhoták P.:

Synthesis of calix[4]arene-cyclen conjugates

Tetrahedron 2006, 62, 5748-5755.

 

Lhoták P., Svoboda J., Stibor I.:

Anion receptors based on ureido-thiacalix[4]arene

Tetrahedron 2006, 62, 1253-1257.

 

 

 
 
 

2005:

 
   

Marecek V., Janchelova H., Stibor I., Budka, J.:

Compact Poly-pyrrole Layers Formed at a Liquid|Liquid Interface

J. Electroanal. Chem. 2005, 575, 293-299

 

Gu R., Depraetere S., Kotek J., Budka J., Wagner-Wysiecka E., Biernat J.F., Dehaen W.:

Anion Recognition by a-arylazo-N-confused Calix[4]pyrroles

Org. Biomol. Chem. 2005, 3, 2921-2923

 

Appelhans D., Smet M., Khimich G., Komber H., Voigt D., Lhoták P., Kuckling D., Voit B.:

Lysine dendrimers based on thiacalix[4]arene core moieties as molecular scaffolds for supramolecular host systems

New. J. Chem. 2005, 29, 1386-1389.

 

Sýkora J., Budka J., Lhoták P., Stibor I., Císařová I.:

Two structural types of 1,3-alternate tetrapropoxycalix[4]arene derivatives in the solid state

Org. Biomol. Chem. 2005, 3, 2572-2578.

 

Lang K., Cuřínová P., Dudič M., Prošková P., Stibor I., Šťastný V., Lhoták P.:

Unusual stoichiometry of urea-derivatized calix[4]arenes induced by anion complexation

Tetrahedron Lett.  2005, 46, 4469-4472.

 

Lang J., Deckerová V., Czernek J., Lhoták P.:

Dynamics of Circular Hydrogen Bond Array in Calix[4]arene in a Non-Polar Solvent

J. Chem. Phys. 2005, 122, 044506.

 

Himl M., Pojarová M., Stibor I., Sýkora J., Lhoták P.:

Stereoselective alkylation of thiacalix[4]arenes

Tetrahedron Lett. 2005, 46, 461-464.

 

 

 
 
 

2004:

 
   

Zlatušková P., Stibor I., Tkadlecová M., Lhoták P.:

Novel anion receptors based on thiacalix[4]arene derivatives

Tetrahedron 2004, 60, 11383-11390.

 

Appelhans D., Šťastný V., Komber H., Voigt D., Voit B., Lhoták P., Stibor I.:

Novel dendritic cores based on thiacalix[4]arene derivatives

Tetrahedron Lett. 2004, 45, 7145-7149.

 

Lhoták P., Stibor I.:

Calixarenes and Their Analogues: Molecular Complexation in Encyclopedia of Supramolecular Chemistry

Atwood J. L., Steed J. W. (Eds.), 2004, pp. 145-152, Marcel Dekker Inc., ISBN: 0-8247-4720-8.

 

Lhoták P.:

Chemistry of thiacalixarenes

Eur. J. Org. Chem. 2004, 1675-1692.

 

Stibor I., Holakovský R., Mustafina A. R., Lhoták P.:

New ligands for enantioselective recognition of chiral carboxylates based on 1,1’-binaphthalene-2,2’-diamine

Collection Czech. Chem. Commun. 2004, 69, 365-383.

 

Šťastný V., Stibor I., Dvořáková H., Lhoták P.:

Synthesis of (thia)calix[4]arene oligomers: Towards calixarene based dendrimers

Tetrahedron 2004, 60, 3383-3391.

 

Dudič M., Lhoták P., Stibor I., Petříčková H., Lang K.:

(Thia)calix[4]arene-porphyrin conjugates: Novel receptors for fullerene complexation with C70 over C60 selectivity

New. J. Chem. 2004, 28, 85-90.

 
    
 

2003:

 
   

Lhoták P., Šmejkal T., Stibor I., Havlíček J., Tkadlecová M., Petříčková H.:

Synthesis of a deep-cavity thiacalix[4]arene

Tetrahedron Lett. 2003, 44, 8093-8097.

 

Lang J., Tošner Z., Lhoták P., Kowalewski J.:

Reorientational dynamics of two isomers of thiacalix[4]arene

Magn. Reson. Chem. 2003, 41, 819-827.

 

Lhoták P., Morávek J., Šmejkal T., Stibor I., Sýkora J.:

Stereoselective oxidation of thiacalix[4]arenes with the NaNO3/CF3COOH system

Tetrahedron Lett.  2003, 44, 7333-7336.

 

Kyrš M., Svoboda K., Lhoták P., Alexová J.:

Synergic solvent extraction of Eu, Sr and Cs into chlorobenzene solutions of the three conformers of tetrathiocalixarene and dicarbollide

Radioanal. Nucl. Chem., 2003, 258, 497-509.

 

Lhoták P., Himl M., Stibor I., Sýkora J., Dvořáková H., Lang J., Petříčková H.:

Conformational behaviour of tetramethoxy-thiacalix[4]arenes: Solution versus solid-state study

Tetrahedron, 2003, 59, 7581-7585.

 

Lhoták P., Zieba R., Hromádko V., Stibor I., Sýkora J.:

Neutral guest complexation with calix[4]arenes preorganised by intramolecular McMurry reaction

Tetrahedron Lett.  2003, 44, 4519-4522.

 

Dudič M., Lhoták P., Petříčková H., Stibor I., Lang K., Sýkora J.:

Calixarene-based metalloporphyrins: Molecular tweezers for complexation of DABCO

Tetrahedron, 2003, 59,  2409-2415.

 

Miyaji H., Dudič M., Tucker J. H. R., Prokeš I., Light M. E., Gelbrich T., Hursthouse M. B., Stibor I., Lhoták P., Brammer L.:

Binding Studies on the Control of the Conformation and Self-Assembly of a Calix[4]arenedicarboxylic Acid through Hydrogen Bonding Interactions

Supramol. Chem. 2003, 15, 385-390.

 

Budka J., Lhoták P., Stibor I., Sýkora J., Císařová I.:

Solid State Calix[4]arene Tubular Assemblies Based on Cation-p Interactions

Supramol. Chem. 2003, 15, 353-357.

 

Dudič M., Lhoták P., Stibor I., Lang K., Prošková P.:

Calix[4]arene-porphyrin conjugates as versatile molecular receptors for anions

Org. Lett., 2003, 5, 149-152.

 

 

 
 
 

2002:

 

 

 

Lhoták P., Himl M., Stibor I., Petříčková H.:

Alkylation of thiacalix[4]arenes

Tetrahedron Lett.  2002, 43, 9621-9624.

 

Kyrš M., Svoboda K., Lhoták P., Alexová J.:

Solvent extraction of europium from nitric acid solutions into chlorobenzene in the presence of calixarenes and dicarbollides

Radioanal. Nucl. Chem. 2002, 254, 455-464.

 

Čajan M., Lhoták P., Lang J., Dvořáková H., Stibor I., Koča J.:

The Conformational Behaviour of Thiacalix[4]arenes: The Pinched Cone – Pinched Cone Transition

J. Chem. Soc., Perkin Trans. 2, 2002, 1922-1929.

 

Lhoták P., Svoboda J., Stibor I., Sykora J.:

Nitration of thiacalix[4]arene derivatives

Tetrahedron Lett. 2002, 43, 7413-7417.

 

Dudič M., Lhoták P., Stibor I., Dvořáková H., Lang K.:

Synthesis and spectroscopic properties of porphyrin-(thia)calix[4]arene conjugates

Tetrahedron, 2002, 58, 7207-7211.

 

Šťastný V., Lhoták P., Michlová V., Stibor I., Sýkora J.:

Novel biscalix[4]arene-based anion receptors

Tetrahedron, 2002, 58, 5475-5482.

 

Gorbatchuk V. V., Tsifarkin A. G., Antipin I. S., Solomonov B. N., Konovalov A. I., Lhoták P., Stibor I.:

Nonlinear Structure-Affinity Relationships for Vapor Guest Inclusion by Solid Calixarenes

Phys. Chem. B, 2002, 106, 5845-5851.

 

Lhoták P., Morávek J., Stibor I.:

Diazo coupling: An alternative method for the upper rim amination of thiacalix[4]arenes

Tetrahedron Lett.  2002, 43, 3665-3668.

 

Křen V., Fišerová A., Weignerová L., Stibor I., Halada P., Přikrylová V., Sedmera P., Pospíšil M.:

Clustered ergot alkaloids modulate celol-mediated cytotoxicity

Bioorganic & Medicinal Chem. 2002, 10, 415-424.

 

Miyaji H., Dudič M., Tucker J. H. R., Prokeš I., Light M. E., Hursthouse M. B., Stibor I., Lhoták P.:

Bis(amidopyridine)-linked calix[4]arenes: a novel type of receptor for dicarboxylic acids

Tetrahedron Lett.  2002, 43, 873-878.

 

Budka J., Lhoták P., Stibor I., Michlová V., Sýkora J., Císařová J.:

A biscalix[4]arene-based ditopic hard/soft receptor for K+/Ag+complexation

Tetrahedron Lett.  2002, 43, 2857-2861.

 

 

 
 
 

2001:

 
   

Budka J., Lhoták P., Michlová V., Stibor I.:

Urea derivatives of calix[4]arene 1,3-alternate: An anion receptor with profound negative allosteric effect

Tetrahedron Lett., 2001, 42, 1583-1586.

 

Lang J., Vlach J., Dvořáková H., Lhoták P., Himl M., Hrabal R., Stibor I.:

Thermal isomerisation of 25,26,27,28-tetrapropoxy-2,8,14,20-tetrathiacalix[4]arene: The first isolation of all four conformers

J. Chem. Soc., Perkin Trans. 2, 2001, 4, 576-580.

 

Lhoták P., Dudič M., Stibor I., Petříčková H., Sýkora J., Hodačová J.:

Unprecedented formation of lactone derivatives in thiacalix[4]arene series

J. Chem. Soc., Chem. Commun., 2001, 8, 731-732.

 

Lhoták P.:

Regioselective and stereoselective oxidation of thiacalix[4]arene tetraacetate: Synthesis of all possible sulfinylcalix[4]arenes

Tetrahedron, 2001, 57, 4775-4779.

 

Havlíček J., Krátký R., Růžičková M., Lhoták P., Stibor I.:

NMR study of the new chiral calix[4]arenes

J. Mol. Struct., 2001, 563, 301-307.

 

Stibor I., Růžičková M., Krátký R., Vindyš M., Havlíček J., Pinkhassik E., Lhoták P., Mustafina A. R., Morozova Y. E., Kazakova E. K., Gubskaya V. P.:

New Calix[4]arene-based amides – their synthesis, conformation, complexation

Coll. Czech. Chem. Commun. 2001, 66, 641-662.

 

Lhoták P., Himl M., Stibor I., Sýkora J., Císařová I.:

Upper rim substitution of thiacalix[4]arene

Tetrahedron Lett., 2001, 42, 7107-7110.

 

Shtarev A. B., Pinkhassik E., Levin M. D., Stibor I., Michl J.:

Partially bridge-fluorinated dimethyl bicyclo[1.1.1]pentane-1,3-dicarboxylates: Preparation and NMR spectra.

J. Am. Chem. Soc. 2001, 123, 3484.

 

Maeda K., Jänchelová H., Lhotský A., Stibor I., Budka J., Mareček V.:

Formation of a polymer layer from monomers absorbed at liquid/liquid interface

Electroanal. Chem. 2001, 516, 103-109

 

Lang K., Kubát P., Lhoták P., Mosinger J., Wagnerová D. M.: 

Photophysical Properties and Photoinduced Electron Transfer Within Host-Guest Complexes of 5,10,15,20-Tetrakis(4-N-methylpyridyl)porphyrin with Water-soluble Calixarenes and Cyclodextrins

Photochem. Photobiol. 2001, 74, 558-565.

 

 

 
 
 

2000:

 
   

Budka J., Tkadlecová M., Lhoták P., Stibor I.:

Synthesis of novel calixsugars: Calix[4]arene-monosaccharide conjugates based on amide bonds

Tetrahedron, 2000, 56, 1883-1887.

 

Lhoták P., Kaplánek L., Stibor I., Lang J., Dvořáková H., Hrabal R., Sýkora J.:

NMR and X-ray analysis of 25,27-dimethoxythiacalix[4]arene: Unique infinite channels in the solid state

Tetrahedron Lett., 2000, 41, 9339-9344.

 

Lhoták P., Šťastný V., Zlatušková P., Stibor I., Michlová V., Tkadlecová M., Havlíček J., Sýkora J.:

Synthesis and 1H NMR complexation study of thiacalix[4]arene tetraacetates

Coll. Czech. Chem. Commun., 2000, 65, 757-771.

 

Hodačová J., Stibor I.:

Synthesis of 2,2´-bipyridines with axially chiral 1,1´-binaphthalene units

Coll. Czech. Chem. Commun. 2000, 65, 83.

 

Synthesis of new binaphthol-based tridentate ligands for enantioselective synthesis

Coll. Czech. Chem. Commun., 2000, 65, 805.

 

Lellek V., Šaman D., Holakovský R. , Lhoták P., Stibor I.:

Straightforward synthesis of axially chiral 1,4-naphthodiazepine derivatives

Synlett, 2000, 11, 1616-1618.

 

Lellek V., Stibor I.:

Dendrimers with inherently axially chiral units

Materials Chem., 2000, 10, 1061.

 

Černovská K., Svoboda J., Stibor I., Glogarová M., Vaněk P., Novotná V.:

Ferroelectric liquid crystals with a fused heterocyclic core

Ferroelectrics, 2000, 241, 231.

 

Čajan M., Damborský J., Stibor I., Koča J.:

Stability of complexes of aromatic amides with bromide anion: Quantitative structure-property relationship

Chem. Inf., Comput. Sci., 2000, 40, 1151.

 

 

 
 
 

1999:

 
   

Lang J., Dvořáková H., Bartošová I., Lhoták P., Stibor I., Hrabal R.:

Conformational flexibily of a novel tetraethylether of thiacalix[4]arene. A comparison with the “classical“ methylene-bridged compounds

Tetrahedron Lett., 1999, 40, 373-376.

 

Dudič M., Lhoták P., Král V., Lang K., Stibor I.:

Synthesis of novel porphyrin-based biscalix[4]arenes

Tetrahedron Lett., 1999, 40, 5949-5952.

 

Budka J., Dudič M., Lhoták P., Stibor I.:

Simple preparation of 5-hydroxy-25,26,27,28-tetraalkyloxycalix[4]arenes: Synthesis of multiple calixarenes

Tetrahedron, 1999, 55, 12647-12654.

 

Amr A. E., Osama I. A. E., Attia A. E., Stibor I.:

Synthesis of new potential intercalators based on chiral pyridine-2,6-dicarboxamides

Coll. Czech. Chem. Commun., 1999, 64, 288.

 

Matušina Z., Olbřímková R., Votavová H., Neumann J., Hradílek M., Souček M., Maloň P., Kodíček M., Stibor I.:

Linear heptapeptides containing DNA-intercalators. Synthesis and interaction with DNA

Coll. Czech. Chem. Commun., 1999, 64, 1419.

 

Čajan M., Stibor I., Koča J.:

Computational Studies on the stability of Amide - Br- Complexes

Phys. Chem., 1999, 103, 3778.

 

Váchal P., Svoboda J., Stibor I., Glogarová M.:

New heterocyclic core structure for chiral liquid crystals

Mol. Cryst. Liq. Cryst., 1999, 328, 367.

 

Adcock W., Blokhin A. V., Elsey G. M., Head N. H., Krstic A. R., Levin M. D., Michl J., Munton J., Pinkhasik E., Robert M., Savéant J.-M., Shtarev A., Stibor I.:

Manifestation of bridghehead-brodgehead interactions in the bicyclo[1.1.1]pentane ring system

J. Org. Chem., 1999, 64, 2618.

 
    
 

1998:

 
   

Lhoták P., Himl M., Pakhomova S., Stibor I.:

Tetraalkylated 2,8,14,20-tetrathia-calix[4]arenes: Novel infinite channels in the solid state

Tetrahedron Lett., 1998, 39, 8915-8918.

 

Vaňura P., Stibor I.:

Extraction of alkaline and alkaline-earth metal cations at synergistic action of bis[undecahydro[7.8]dicarbaundecaborato(2-)cobaltate(1-) and substituted calix[n]arenes in nitrobenzene

Coll. Czech. Chem. Commun., 1998, 63, 2009.

 

Hovorka M., Smíšková I., Holakovský R., Beran J., Stibor I.:

Chiral tridentate ligands based on 3-substituted binapthols and derived complex hydrides of aluminium

Pure&Appl.Chem., 1998, 70, 415.

 

Kašpar M., Hamplová V.,Pakhomov S.A., Bubnov A.M., Giuttard F., Sverenyák H., Stibor I., Vaněk M., Glogarová M.:

New series of ferroelectric liquid crystals with four ester groups

Liquid Crystals, 1998, 24, 599-605.

 

Kozmík V., Lhoták P., Odlerová Ž, Paleček J.:

Azachalcone derivatives and their bis substituted analogs as novel antimycobacterial agents

Coll. Czech. Chem. Commun., 1998, 63, 698-712.

 

Pakhomov S., Kašpar M., Hamplová V., Bubnov A. M., Sverenyák H., Glogarová M., Stibor I.:

Synthesis and mesomorphic properties of (S)-lactic acid derivatives containing several ester linkages in the core

Ferroelectrics, 1998, 212, 341-8.

 

Mareček V., Lhotský A., Holub K., Stibor I.:

Surface complex formation at the water/1,2-dichloroethane interface

Electrochimica Acta, 1998, 44, 155-9.

 

Pinkhassik E., Sidorov V., Stibor I.:

Calix[4]arene-based receptors with hydrogen-bonding groups immersed into a large cavity

J. Org. Chem., 1998, 63, 9644-51.

 

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Medicinal Chemistry and Glycochemistry

We work on the borders of organic, bioorganic and medicinal chemistry. Our main interest is the synthesis of ligands for lectin receptors and their use in diagnostics and drug targeting. In addition, we synthesize ligands for the visualization of G-quadruplexes and we have just started a new project on the synthesis of agonists of muscarine receptors.

 In our lab, we do mostly organic synthesis, purification of the compounds and their characterization. The preparation of nanoparticles as well as all biological testing are done by our collaborators.

 In September 2021, we became an official Max Planck Partner Group. This prestigious partnership enables us to run several projects in the field of glycochemistry.

More details about the projects can be found in the Research section.

 ◳ Group picture 2021 reaction scheme

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 ◳ Group picture 2021 reaction scheme

Group leader:  Dr. Petra Ménová
   
Technician: Květa Bártová
   
PhD students:

Fabricio Ramírez Cortés

Rohit Chavan
Undergraduate students:   

Jiří Ledvinka

Kateřina Jochová

Vojtěch Kramný

Ondřej Daněk

Jan Wohlgemuth

Jakub Schimmer

Martin Brokeš

Michal Čotek

   
Alumni:   

Morgane Moinard (FR)

Vojtěch Musil

Dmytro Makarov (UA)

Romane Vizier (FR)

Pauline Mornat (FR)

 

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Projects

 

Synthesis of inhibitors of DC-SIGN receptor

DC-SIGN is a C-type lectin receptor present on the surface of dendritic cells and macrophages. It binds to carbohydrate structures found on the surface of numerous pathogens: viruses (HIV, ebola, cytomegalovirus), bacteria (M. tuberculosis, S. pneumoniae), fungi (C. albicans), and parasites (Leishmana). The surface of these pathogens is typically rich in mannose and fucose which are natural DC-SIGN ligands. Upon binding, DC-SIGN can mediate the uptake of the pathogen into the dendritic cell and launch an immune response. Hence, DC-SIGN inhibitors could act as anti-infective agents.

 The primary carbohydrate binding site of DC-SIGN is rather shallow and hydrophobic and as such is not a good target for medicinal chemistry. Recent studies have shown that apart from the primary carbohydrate binding site, DC-SIGN harbours five secondary binding sites available to accommodate small drug-like molecules (Figure 1).

Figure 1. DC-SIGN receptor, primary carbohydrate binding site (yellow) and secondary binding sites I–V. Picture taken from Aretz, J. et al.: Angew. Chem. Int. Ed. 2017, 56, 7292–7296.

 

In this project, we synthesize substituted mannosides and fucosides which can interact with both, the primary and secondary binding site (Figure 2a). In parallel, we synthesize non-carbohydrate ligands which interact with the secondary binding sites and upon binding modulate the interaction of carbohydrates with the primary carbohydrate binding site (Figure 2b). To synthesize these compounds, we use an approach called fragment-based drug discovery.

Figure 2. Overview of the synthesized DC-SIGN ligands. a) DC-SIGN inhibitors based on D-mannose and l-fucose; b) non-carbohydrate inhibitors binding to the secondary binding sites.

 

 

Preparation of nanoparticles with DC-SIGN-targeting ligands

We use the synthesized DC-SIGN ligands to modify the surface of nanoparticles, in particular fluorescent nanodiamonds and liposomes (Figure 3). Fluorescent nanodiamonds can be used for the visualization of metastases in sentinel lymphatic nodes. Tumour-associated macrophages (TAMs) gather in the vicinity of metatases. Upon binding of the fluorescent nanodiamonds modified with DC-SIGN ligand to TAMs, the nanoparticles are internalized and their fluorescence properties enable the visualisation of the macrophages and thus indirectly of the metastases.

 Liposomes modified with DC-SIGN ligands can be used for targeted delivery of therapeutic compounds to dendritic cells.

Figure 3. Nanoparticles modified with DC-SIGN ligands. a) Fluorescent nanodiamonds for the visualization of metastases; b) liposomes for targeted delivery of therapeutic compounds into dendritic cells.

 

 

Synthesis of ligands for ASGPR receptor and their use in the treatment of hepatitis B

ASGPR is a C-type lectin receptor which specifically recognizes ligands with terminal galactose or N-acetylgalactosamine. It is found almost exclusively on hepatocytes and is already clinically used for ASGPR-targeted drug delivery to the liver. Our aim is to prepare lipid nanoparticles modified with selective ASGPR ligands (Figure 4) and use these nanoparticles to transport CRISPR/Cas9 system into the liver. Several studies have already confirmed the application of CRISPR/Cas9 as a feasible approach to eradicate the hepatitis B virus DNA and thus help treat hepatitis B.

Figure 4. Lipid nanoparticles modified with ASGPR ligands.

 

 

Synthesis of ligands for G-quadruplex visualization

In collaboration with ICMUB CNRS Dijon, France, we synthesize ligands for the visualization of G-quadruplexes. Our aim is to prepare twice-as-smart fluorescent probes that act both as a smart quadruplex ligand (i.e., that assembles only in the presence of its native G-quadruplex target) and a smart fluorescent probe (i.e., the fluorescence of which is turned on only upon interaction with its target). A similar compound, N-TASQ, allowed for the very first visualization of G-quadruplexes in living human cells and since then has been used in oncology and neurology.

Figure 5. Twice-as-smart probes for the visualization of G-quadruplex. Picture taken from Laguerre, A. et al.: J. Am. Chem. Soc. 2015, 137, 8521–8525.

 

Synthesis of agonists of muscarine receptor

In collaboration with the group of neurochemistry from the Institute of Physiology CAS, we have just started working on the synthesis of agonists of muscarine receptors based on tetrahydropyridine. These compounds are promising agents for the treatment of neuropathies.

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Dr. Ménová:

  • Medicinal chemistry (ENG)
  • Organic chemistry: laboratory I (ENG)
  • Základy farmakochemie (Fundamentals of chemistry of pharmaceuticals, CZ)
  • Organická chemie A, B – seminář (Organic chemistry A, B – seminar, CZ)
  • Laboratoř organické chemie I, II (Laboratory of organic chemistry I, II, CZ)
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Papers

  1. Ménová: ASGPR a DC-SIGN: C-lektinové receptory se slibným potenciálem v medicinální chemii. Chem. Listy 2021, 115, 126–133.

 

Bachelor theses

Jochová Kateřina: Modified nanoparticles for DC-SIGN targeting (2021)

Ledvinka Jiří: Synthesis of mannose-based DC-SIGN antagonists (2020)

Musil Vojtěch: Synthesis of quinoxalinone-based inhibitors of DC-SIGN receptor (2020)

Wohlrábová Lucie: Chelating lipids for optical quantum nanosensors (2019)

Makarov Dmytro: Syntéza substituovaných chinolonů jako potenciálních inhibitorů DC-SIGN receptoru (2018)

 

Master theses

Makarov Dmytro: Synthesis of quinolone-based inhibitors of DC-SIGN receptor (2020)

Mornat Pauline: Synthesis of mannose-based DC-SIGN inhibitors bearing fluorinated arene moiety (2019)

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Medicinal chemistry of natural compound inspired scaffolds

The research group led by Mgr. et Mgr. Pavla Perlíková, Ph.D.

We are looking for PhD students. More information here.


Our research is focused on development of migrastatics using natural product-inspired scaffolds. We also work on development of antiparasitic compounds, namely with activity against trypanosomatids. In our projects, we are combining synthesis of complex molecules and medicinal chemistry.

More details about the projects can be found in the Research section.

 ◳ Web2024 (png) → (originál)

The research group led by Pavla Perlíková

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Publications

Formánek, B.; Dupommier, D.; Volfová, T.; Rimpelová, S.; Škarková, A.; Herciková, J.; Rösel, D.; Brábek, J.; Perlíková, P.: Synthesis and migrastatic activity of cytochalasin analogues lacking a macrocyclic moiety. RSC Med. Chem. 2024, 15, 322-343. DOI: 10.1039/D3MD00535F

 

You can find older publications HERE.

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PhD topics

Two PhD topics in organic/medicinal chemistry are announced for 2024/2025, which will be funded by ongoing grant projects. Topics can be carried out within Chemistry or Drugs and Biomaterials study programmes. Interested candidates should contact the group leader directly.

 

Synthesis of inhibitors of the Arp2/3 complex

Migrastics represent a new approach to cancer treatment. Their aim is to prevent metastasis of cancer cells. One suitable target for the development of migrastatics is the Arp2/3 protein complex, which initiates actin polymerization at microfilament branching sites. In this work, inhibitors of the Arp2/3 complex will be prepared based on virtual screening data. The relationship between their structure and activity will be studied and their pharmacological properties will be further optimized.

 

Synthesis of inhibitors of transcription factors involved in metabolic diseases

Transcription factors play an important role in the regulation of gene expression. Deregulation of key protein synthesis leads to a variety of metabolic diseases. The aim of this work is to use rational drug design to prepare suitable inhibitors of selected transcription factors and to further investigate the structure-activity relationship.

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Pavla Perlíková
Building ZB3, room 206
+ 420 220 44 2039
Pavla.Perlikova@vscht.cz

Lab
Building A, room 262
+ 420 220 44 4276

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Research topics of the group

Migrastatics

Metastasis accounts for more than 90% of cancer-related deaths. Despite recent advances in cancer therapies, the majority of patients with advanced-stage solid tumors die as a result of metastatic disease. Migrastatics represent a new concept of drugs with a great potential to improve the outcome of the current cancer treatment strategies by inhibiting metastatic behavior of cancer cells.

Our goal is to use rational design to synthesize new natural compound analogs with antimetastatic activity. We study structure-activity relationships. Our protein target is actin and actin polymerization regulators, such as the Arp2/3 complex. Antimetastatic activity screening of the new compounds is performed in collaboration with Prof. Jan Brábek group at BIOCEV (Vestec, Czechia).

 ◳ WebEN2023Migrastatika (png) → (originál)

Projects:

2023-2027:      Development of actin polymerization inhibitors as potential migrastatics (GAČR)

2021-2022:      Development of actin-targeting compounds with anti-metastatic effect (Dagmar Procházková Fund)


Transcription factor inhibitors

The regulation of cell signaling is one of the most common mechanisms of action for drugs. It is possible to affect cell receptors as well as signal transduction within the cell. Gene expression can also be affected indirectly. However, direct regulation of protein expression by targeting transcription factors is challenging. So far, only a small fraction of them, the so-called nuclear receptors, have been exploited because most transcription factors do not contain binding sites for small molecules.

In our group, we are working on the rational design of inhibitors of other transcription factors involved in metabolic disorders such as diabetes, obesity and infertility. In this project we collaborate within the VSČHT with the groups of prof. Andrea Brancale and Prof. Daniel Svozil.

Projects:

2024-2028:      NETPHARM: New technologies for translational research in pharmaceutical sciences (OP JAK)

 

Antiparasitic compounds


Trypanosomatids are causative agents of several diseases transmitted by insects: Chagas disease (Trypanosoma cruzi), human african trypanosomiasis known as „sleeping sickness“ (Trypanosoma b. gambiense, Trypanosoma b. rhodesiense) and leishmaniasis (Leishmania sp.). The current treatment of these diseases is complicated. Therefore, we study natural compounds, elucidate their mechanism of action and synthesize their analogs for further development as potential drugs. New compounds are developed in collaboration with the group of Prof. Vyacheslav Yurchenko (University of Ostrava).

 ◳ AntiP (png) → (šířka 450px)

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People in research group

Group leader:

Postdoc researcher:

  • Dorian Dupommier
  •  Wim Dehaen

PhD students:

  • Žaneta Javorská
  • Michal Trojan

Students:

  • Daniel Kozový
  • Jiří Ferenczei
  • Veronika Švecová
  • Matěj Říha
  • Artem Lobanov

Laboratory staff:

Michaela Kadlecová

Alumni:

Bedřich Formánek

Vilém Blahout

Tereza Kubátová

  ◳ 2023 12 21 Perlíková skupina 1080px 001 (jpg) → (originál)

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The page has not been synthesized yet..

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Staff:

PhD Students:

  • MSc. Kvetoslava Bajzíková
  • MSc. Anna Poryvai
  • MSc. Jana Herciková
  • MSc. Michal Šmahel
 

Undergraduate Students:

Master Study, 2nd year

  • Bc. Tereza Černá
  • Bc. Natálie Kolderová
  • Bc. Martin Paškan
  • Bc. Karolína Zvolská

Bachelor Study, 3rd year

  • Jaroslav Cerman
  • Diana Jágerová
  • Žaneta Javorská
  • Tereza Ludvíková
  • Eva Tetenková
  • Adam Vít

Bachelor Study, 2nd year

  • Jakub Dávid Malina
  • Anna Rejzková

Alumni:

  • Ing. Miloslav Nič, Ph.D.
  • Ing. Pavel Pihera, CSc.
  • Ing. Miroslav Terinek, Ph.D.
  • Ing. Marie Havelková
  • Ing. Petr Váchal, Ph.D.
  • Ing. Kateřina Černovská, Ph.D.
  • Ing. Kateřina Dudová
  • Ing. Petr Vodička, Ph.D.
  • Ing. Lech Mrózek, Ph.D.
  • Ing. Bedřich Košata, Ph.D.
  • Ing. Marie Mézlová, Ph.D.
  • Ing. Michal Rejňák
  • Ing. Milan Kurfürst, Ph.D.
  • Ing. Aleš Machara, Ph.D.
  • Ing. Martin Kuchař, Ph.D.
  • Ing. Michal Kohout, Ph.D.
  • Ing. Anna Kovářová, Ph.D.
  • Ing. Petr Hadrava
  • Ing. Adam Henke, Ph.D.
  • Ing. Jiří Žurek, Ph.D.
  • Ing. Petr Polášek
  • Ing. Petr Špaček
  • Ing. Arnošt Seidler
  • Ing. Lucie Řehová
  • Ing. Svatopluk Světlík
  • Ing. Jiří Veselý
  • Ing. Michal Pozník
  • Ing. Michal Májek
  • Ing. Ondřej Píša
  • Ing. Eva Rodinová
  • Ing. Kvetoslava Bajzíková
  • Ing. Martin Horčic
  • Ing. Jiří Tůma
  • Ing. Anna Poryvai
  • Ing. Lenka Pallová
  • Ing. Helena Skopalová
  • Ing. Tomáš Hodík
  • Ing. Tereza Prausová
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2019

  • Jing, H.; Xu, M.; Xiang, Y.; Wang, E.; Liu, D.; Poryvai, A.; Kohout, M.; Éber, N.; Buka, A.:
    Light tunable gratings based on flexoelectric effect in photoresponsive bent-core nematics.
    Adv. Opt. Mater. 2019, 1801790 DOI: 10.1002/adom.201801790

  • Pokluda, A.; Kohout, M.; Chudoba, J.; Krupička, M.; Cibulka, R.:
    Nitrosobenzene: Reagent for the Mitsunobu esterification reaction.
    ACS Omega 2019, 4, 5012-5018 DOI: 10.1021/acsomega.8b03551

  • Spálovská, D.; Maříková, T.; Kohout, M.; Králík, F.; Kuchař, M.; Setnička, V.:
    Methylone and pentylone: Structural analysis of new psychoactive substances.
    Forensic Toxicol. 2019, 37, 366-377 DOI: 10.1007/s11419-019-00468-z

  • Poryvai, A.; Bubnov, A.; Pociecha, D.; Svoboda, J.; Kohout, M.:
    The effect of the length of terminal n-alkyl carboxylate chain of self-assembling and photosensitive properties of chiral lactic acid derivatives.
    J. Mol. Liq. 2019, 275, 829-838 DOI: 10.1016/j.molliq.2018.11.058

  • Geibel, C.; Dittrich, K.; Woiwode, U.; Kohout, M.; Zhang, T.; Lindner, W.; Lämmerhofer, M.:
    Evaluation of superficially porous particle based zwitterionic chiral ion exchangers against fully porous particle benchmarks for enantioselective ultra-high performance liquid chromatography.
    J. Chromatogr. A 2019, 1603, 130-140 DOI: 10.1016/j.chroma.2019.06.026

  • Poryvai, A.; Vojtylová-Jurkovičová, T.; Šmahel, M.; Kolderová, N.; Tomášková, P.; Sýkora, D.; Kohout, M.:
    Determination of optical purity of lactic acid-based chiral liquid crystals and corresponding building blocks by chiral high-performance liquid chromatography and supercritical fluid chromatography.
    Molecules 2019, 24, 1099 DOI: 10.3390/molecules24061099

  • Tlustý, M.; Eigner, V.; Babor, M.; Kohout, M.; Lhoták, P.:
    Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds.
    RSC Adv. 2019, 9, 22017-22030. DOI: 10.1039/C9RA05075B

2018

  • Jurásek, B.; Králík, F.; Rimpelová S.; Čejka, J.; Setnička, V.; Ruml, T.; Kuchař, M.; Kohout, M.:
    Synthesis, Absolute Configuration and in vitro Cytotoxicity of Deschloroketamine Enantiomers: Rediscovered and Abused Dissociative Anaesthetic
    New. J. Chem. 2018, 42, 19360-19368 DOI:
    10.1039/c8nj03107j

    COVER

    New. J. Chem. 2018, 42, 19360-19368 DOI: 10.1039/c8nj03107j

  • Schmitt, K.; Woiwode, U.; Kohout, M.; Zhang, T.; Lindner, W.; Lämmerhofer, M.:
    Comparison of small size fully porous particles and superficially porous particles of chiral anion-exchange type stationary phases in ultra-high performance liquid chromatography: effect of particle and pore size on chromatographic efficiency and kinetic performance
    J. Chromatogr. A 2018, 1569, 149-159 DOI:10.1016/j.chroma.2018.07.056

  • Spálovská, D.; Kralik, F.; Kohout, M.; Jurasek, B.; Habartová, L.; Kuchar, M.; Setnicka, V.: 
    Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies 
    Chirality 2018, 30, 548-559 DOI:10.1002/chir.22825

  • Wolrab, D.; Kohout, M.:
    Multimodální stacionární fáze pro kapalinovou chromatografii, způsob jejich přípravy a jejich použití.
    Národní patent č. 307339, číslo přihlášky 2017-193, datum udělení 2.5.2018, datum zveřejnění 13.6.2018.

  • Kohout, M.; Wernisch, S.; Tuma, J.; Hettegger, H.; Picha, J.; Lindner W.: 
    Effect of different immobilization strategies on chiral recognition properties of Cinchona-based anion exchangers 
    J. Sep. Sci. 2018, 41, 1355-1364 DOI:10.1002/jssc.201701213

  • Bajtai, A.; Fekete, B.; Palkó, M.; Fülöp, F.; Lindner, W.; Kohout, M.; Ilisz, I.; Péter, A.: 
    Comparative study on the liquid chromatographic enantioseparation of cyclic β-amino acids and the related cyclic β-aminohydroxamic acids on Cinchona alkaloid-based zwitterionic chiral stationary phases 
    J. Sep. Sci. 2018, 41, 1216-1223 DOI:10.1002/jssc.201701190

  • Sardella, R.; Macchiarulo, A.; Urbinati, F.; Ianni, F.; Carotti, A.; Kohout, M.; Lindner, W.; Péter, A.; Ilisz, I.: 
    Exploring the enantiorecognition mechanism of Cinchona alkaloid-based zwitterionic chiral stationary phases and the basic trans-paroxetine enantiomers 
    J. Sep. Sci. 2018, 41, 1199-1207 DOI:10.1002/jssc.201701068

  • Tuma, J.; Kohout, M.: 
    Silica gel-immobilized multidisciplinary materials applicable in stereoselective organocatalysis and HPLC separation 
    RSC Adv. 2018, 8, 1174-1181 DOI:10.1039/c7ra12658a

  • Kozmik, V.; Rodinová, E.; Prausová, T.; Svoboda, J.; Novotná, V.; Pociecha, D.:
    Mesogens with central naphthalene core substituted at various positions 
    Liq. Cryst. 2018, 45, 744-756 DOI: 10.1080/02678292.2017.1380238

  •  Bajzíková, K.; Vesely, J.; Kozmik, V.; Svoboda, J.; Novotná, V.; Pociecha, D.:
    Thiophene central core for the design of bent-shaped liquid crystals 
    J. Mol. Liq. 2018, 267, 496-503 DOI:10.1016/j.molliq.2018.02.009

  • Horcic, M.; Svoboda, J.; Novotná, V.; Pociecha, D.; Gorecka, E.:
    Bent-core dimers with top-to-bottom linkage between central units 
    RSC Adv. 2018, 8, 22974-22985 DOI: 10.1039/c8ra04108c

  • Marz, M.; Kohout, M.; Nevesely, T.; Chudoba, J.; Prukala, D.; Nizinski, S.; Sikorski, M.; Burdzinski, G.; Cibulka, R.:
    Azodicarboxylate-free esterification with triphenylphosphine mediated by flavin and visible light: method development and stereoselectivity control
    Org. Biomol. Chem. 2018, 16, 6809-6817 DOI:10.1039/C8OB01822G

2017

  • Maixner, J.; Jurásek, B.; Kohout, M.; Kuchar, M.; Kacer, P.:
    X-ray powder diffraction data for (S)-Deschloroketamine hydrochloride, C13H18ClNO.
    Powder Diffr. 2017, 32, 193-195. DOI:10.1017/S0885715617000586

  • Bajzíková, K.; Svoboda, J.; Novotná, V.; Pociecha, D.; Gorecka E.:
    Bent-core mesogens with an aromatic unit at the terminal position
    New J. Chem. 2017, 41, 4672-4679 DOI: 10.1039/C6NJ03908A

  • Žurek, J.; Svobodová, E.; Šturala, J.; Dvořáková, H.; Svoboda, J.; Cibulka, R.:
    Chiral ethylene-bridged flavinium salts: The stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties
    Tetrahedron Asymmetry 2017, asap DOI:10.1016/j.tetasy.2017.10.029

  • Dobrovolny, K.; Ulbrich, P.; Svecova, M.; Rimpelova, S.; Malincik, J.; Kohout, M.; Svoboda, J.; Bartunek, V.: 
    Copper nanoparticles in glycerol-​polyvinyl alcohol matrix: In situ preparation, stabilization and antimicrobial activity
    Journal of Alloys and Compounds 2017, 697, 147-155 DOI:10.1016/j.jallcom.2016.12.144

  • Kolderova, N.; Nevesely, T.; Sturala, J.; Kuchar, M.; Holakovsky, R.; Kohout, M.:
    Enantioseparation of chiral sulfoxides on amylose-​based columns: comparison of normal phase liquid chromatography and supercritical fluid chromatography
    Chromatographia 2017, 80, 547-557 DOI: 10.1007/s10337-016-3234-6

  • Kohout, M.; Alaasar, M.; Poryvai, A.; Novotna, V.; Poppe, S.; Tschierske, C.; Svoboda, J.: 
    Photosensitive bent-​core liquid crystals based on methyl substituted 3-​hydroxybenzoic acid
    RSC Advances 2017, 7, 35805-35813 DOI:10.1039/C7RA05632J

  • Wolrab, D.; Fruehauf, P.; Gerner, C.; Kohout, M.; Lindner, W.: 
    Consequences of transition from liquid chromatography to supercritical fluid chromatography on the overall performance of a chiral zwitterionic ion-​exchanger
    Journal of Chromatography A 2017, 1517, 165-175 DOI:10.1016/j.chroma.2017.08.022

  • Pallova, L.; Kozmik, V.; Kohout, M.; Svoboda, J.; Novotna, V.; Pociecha, D.: 
    Bent-​core liquid crystals with a 2-​substituted 3-​hydroxybenzoic acid central core
    Liquid Crystals 2017, 44, 1306-1315 DOI: 10.1080/02678292.2016.1276981

  • Tlusty, M.; Slavik, P.; Kohout, M.; Eigner, V.; Lhotak, P.:
    Inherently Chiral Upper-Rim-Bridged Calix[4]arenes Possessing a Seven Membered Ring
    Org. Lett. 2017, 19, 2933-2936 DOI:10.1021/acs.orglett.7b01170

  • Miksatko, J.; Eigner, V.; Kohout, M.; Lhotak, P.:
    Regio-/stereoselective Formation of Monosulfoxides from Thiacalix[4]arenes in All Possible Conformations
    Tetrahedron Letters 2017, 58, 1687–1691 DOI:10.1016/j.tetlet.2017.03.043

  • Horčic, M.; Kohout, M.; Svoboda, J.; Novotna, V.; Pociecha, D.; Gorecka, E.:
    Core-to-core Dimers Forming Switchable Mesophase
    Chem.  Commun. 2017, 53, 2721-2724 DOI:
    10.1039/C6CC09983A

  • März, M.; Chudoba, J.; Kohout, M.; Cibulka, R.:
    Photocatalytic Esterification under Mitsunobu Reaction Conditions Mediated by Flavin and Visible Light
    Org. Biomol. Chem. 2017, 15, 1970-1975 DOI:10.1039/C6OB02770A

2016

  • Bajzikova, K.; Kohout, M.; Tarabek, J.; Svoboda, J.; Novotna, V.; Vejpravova, J.; Pociecha, D.; Gorecka, E.:
    All-organic liquid crystalline radicals with a spin unit in the outer position of a bent-core system
    J. Mater. Chem. C 2016, 4, 11540-11547 DOI:10.1039/C6TC04346A

  • Tůma, J.; Kohout, M.; Svoboda, J.; Novotná, V.; Pociecha, D.:
    Bent-core liquid crystals based on 6-substituted 3-hydroxybenzoic acid: the role of substitution and linkage group orientation on mesomorphic properties
    Liq. Cryst. 2016, 43, 1889-1900 DOI:10.1080/02678292.2016.1230789

  • Kohout, M.; Vandenbussche, J.; Roller, A.; Tůma, J.; Boqaerts, J.; Bultinck, P.; Herrebout, W.; Lindner, W.:
    Absolute configuration of the antimalarial erythro-mefloquine - vibrational dichroism and X-ray diffraction studies of mefloquine and its thiourea derivative
    RSC Advances 2016, 6, 81461-81465 DOI:10.1039/C6RA19367F 

  • Kohout, M.; Bubnov, A.; Šťurala, J.; Novotná, V.; Svoboda, J.:
    Effect on alkyl chain length in the terminal ester group on mesomorphic properties of new chiral lactic acid derivatives
    Liq. Cryst. 2016, 43, 1472-1485 DOI:10.1080/02678292.2016.1185170

  • Grecsó, N.; Kohout, M.; Carotti, A.; Sardella, R.; Natalini, B.; Fülöp, F.; Lindner, W.; Péter, A.; Ilisz, I.: 
    Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds
    J. Pharm. Biomed. Anal. 2016, 124, 164-173 DOI:10.1016/j.jpba.2016.02.043

  • Wolrab, D.; Frühauf, P.; Moulisova, A.; Kuchar, M.; Gerner, C.; Lindner, W.; Kohout, M.:
    Chiral separation of new designer drugs (Cathinones) on chiral ion-exchange type stationary phases
    J. Pharm. Biomed. Anal. 2016, 120, 306-315 DOI:10.1016/j.jpba.2015.12.023

  • Tůma, J.; Kohout, M.; Svoboda, J.; Novotná, V.; Pociecha, D.: 
    Bent-shaped liquid crystals based on 4-substituted 3-hydroxybenzoic acid central core - Part II 
    Liq. Cryst. 2016, 43, 547-563 DOI: 10.1080/02678292.2015.1125535

  • Slavik, P.; Kohout, M.; Böhm, S.; Eigner, V.; Lhotak, P.:
    Synthesis of 
    Inherently Chiral Calixarenes via Direct Mercuration of the Partial Cone Conformation 
    Chem. Comm. 2016, 52, 2366-2360 DOI:10.1039/C5CC09388K

2015

  • Trišović, N.; Antanasijević, J.; Tóth-Katona, T.; Kohout, M.; Salamonczyk, M.; Sprunt, S.; Jákli, A.; Fodor-Csorba, K.: Azo-containing asymmetric bent-core liquid crystals with modulated smectic phase RSC Adv. 2015, 5, 64886-64891. DOI: 10.1039/c5ra09764a
     
  • Kohout, M.; Bielec, B.; Steindl, P.; Trettenhahn, G.; Lindner, W.: Mechanistic aspects of the direct C-acylation of cyclic 1,3-diones with various unactivated carboxylic acids Tetrahedron 2015, 71, 2698-2707. DOI: 10.1016/j.tet.2015.03.037
     
  • von Koschitzky, I.; Gerhardt, H.; Lämmerhofer, M.; Kohout, M.; Gehringer, M.; Laufer, S.; Pink, M.; Schmitz-Spanke, S.; Strube, C.; Kaiser, A.: New insights into novel inhibitors against deoxyhypusine hydrolase from plasmodium falciparum: compounds with an iron chelating potential Amino Acids 2015, 47, 1155-1166. DOI: 10.1007/s00726-015-1943-z
     
  • Kohout, M.; Kozmík, V.; Slabochová, M.; Tůma, J.; Svoboda, J.; Novotná, V.; Pociecha, D.: Bent-shaped liquid crystals based on 4-substituted 3-hydroxybenzoic acid central core Liq. Cryst. 2015, 42, 87-103. DOI: 10.1080/02678292.2014.965232
     
  • Kozmík, V.; Poznik, M.; Svoboda, J.; Frere, P.:
    Dithieno[3,2-b:2',3'-d]furan as a new building block for fused conjugated systems
    Tetrahedron Lett. 201556, 6251-6253. DOI:10.1016/j.tetlet.2015.09.107
     

2014

  • Lo Ch., Doucoure B. I., Aaron J.-J., Svoboda J., Kozmík V., Brochon J.-C., Henry H., Capochichi M.: Synthesis and optical properties of new fluorescent substituted thieno[3,2-b]indole derivatives. Spectrochim. Acta A, Molecular and Biomolecular Spectroscopy 2014, 120C, 47-54. DOI: 10.1016/j.saa.2013.09.134
     
  • Kovářová A., Světlík S., Kozmík V., Svoboda J., Novotná V., Pociecha D., Gorecka E., Podoliak N.: Unusual polymorphism in new bent-shaped liquid crystals with hydroxybiphenylcarboxylic acid central unit. Beil. J. Org. Chem. 2014, 10, 794-807. DOI: 10.3762/bjoc.10.75
      
  • Olšinová M., Jurkiewicz P., Pozník M., Šachl R., Prausová T., Hof M., Kozmík V., Teplý F., Svoboda J., Cebecauer M.: Di- and tri-oxalkyl derivatives of boron dipyrromethene (BODIPY) rotor dye in lipid bilayers. PhysChemChemPhys. 2014, 16, 10688-10697. DOI: 10.1039/C4CP00888J
     
  • Hetteger H., Kohout M., Mimini V., Lindner W.: Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry. J. Chromatogr. A 2014, 1337, 85-94. DOI: 10.1016/j.chroma.2014.02.026

 

2013

  • Machara A., Svoboda J.: Thiophenium-ylides: synthesis and reactivity. Chem. Papers 2013, 67, 59-65. DOI: 10.2478/s11696-012-0222-7
     
  • Kohout M., Tůma J., Svoboda J., Novotná V., Gorecka E., Pocicha D.: 3-Hydroxycinnamic acid - a new central core for the design of bent-shaped liquid crystals. J. Mater. Chem. C 2013, 1, 4962-4969. DOI: 10.1039/C3TC30664J
     
  • Novotná V., Baumeister U., Kohout M., Svoboda J.: Mesomorphic properties of a bent-shaped liquid crystalline monomer. Phase Trans. 2013, 86, 503-515. DOI: 10.1080/01411594.2012.702279
     
  • Horčic M., Kozmík V., Svoboda J., Novotná V., Pociecha D.: Transformation from a rod-like to a hockey-stick-like and bent-shaped molecule in 3,4'-disubstituted azobenzene-based mesogens. J. Mater. Chem. C 2013, 1, 7560-7567. DOI: 10.1039/C3TC31593B
     
  • Seidler A., Svoboda J., Dekoj V., Chocholoušová J., Vacek J., Stará I. G., Starý I.: The synthesis of pi-electron molecular rods with a thiophene or thieno[3,2-b]thiophene core units and sulphur alligator clips. Tetrahedron Lett. 2013, 54, 2795-2798. DOI: 10.1016/j.tetlet.2013.03.084
     
  • Novotná V., Glogarová M., Kozmík V., Svoboda J., Hamplová V., Kašpar M., Pociecha D.: Frustrated phases induced in binary mixtures of hockey-stick and chiral rod-like mesogens. Soft Matter 2013, 9, 647-653. DOI: 10.1039/C2SM27194J
     
  • Wolrab D., Macíková P., Boras M., Kohout M., Lindner W.: Strong cation exchange chiral stationary phase - A comparative study in high-performance liquid chromatography and subcritical fluid chromatography. J. Chromatogr. A 2013, 1317, 59-66. DOI: 10.1016/j.chroma.2013.08.037
     
  • Gargano A. F. G., Buchinger S., Kohout M., Lindner W., Lämmerhofer M.: Single-step Ugi multicomponent reaction for the synthesis of phosphopeptidomimetics. J. Org. Chem. 2013, 78, 10077-10087. DOI: 10.1021/jo401372x
     
  • Wernisch S., Bisi F., Cazzato A. S., Kohout M., Lindner W.: 2-Acyl-dimedones as UV-active protective agents for amino acids: enantiomer separations of the derivatives on chiral anion exchangers. Anal. Bioanal. Chem. 2013, 405, 8011-8026. DOI: 10.1007/s00216-013-6932-z
     
  • Gargano A. F. G., Kohout M., Macíková P., Lämmerhofer M., Lindner W.: Direct high-performance liquid chromatographic separation of free alpha-, beta- and gamma-aminophosphonic acids employing cinchona-based chiral zwitterionic ion exchangers. Anal. Bioanal. Chem. 2013, 405, 8027-8038. DOI: 10.1007/s00216-013-6938-6
     
  • Wolrab D., Frühauf P., Kohout M., Lindner W.: Click chemistry immobilization strategies in the development of strong cation exchanger chiral stationary phases for HPLC. J. Sep. Sci. 2013, 36, 2826-2837. DOI: 10.1002/jssc.201300559
     
  • Wolrab D., Kohout M., Boras M., Lindner W.: Strong cation exchange-type chiral stationary phase for enantiseparation of chiral amines in subcritical fluid chromatography. J. Chromatogr. A 2013, 1289, 94-104. DOI: 10.1016/j.chroma.2013.03.018

 

2012

  • Mallet C., Savitha G., Allain M., Kozmík V., Svoboda J., Fre?re P., Roncali J.: Synthesis and electronic properties of D-A-D triads based on 3-alkoxy-4-cyanothiophene and benzothienothiophene blocks. J. Org. Chem. 2012, 77, 2041-2046.
  • Kovářová A., Kozmík V., Svoboda J., Novotná V., Glogarová M., Pociecha D.: Naphthalene-based bent-shaped liquid crystals with a semifluorinated terminal chain. Liq. Cryst. 2012, 39, 755-767.
  • Kozmík V., Horčic M., Svoboda J., Novotná V., Pociecha D.: 3-Aminophenol based bent-shaped liquid crystals with an amide linking group. Liq. Cryst. 2012, 39, 943-955.
  • Kohout M., Kählig H., Wolrab D., Roller A., Lindner W.: Novel chiral selector based on mefloquine - A comparative NMR study to elucidate intermolecular interactions with acidic chiral selectands. Chirality 2012, 24, 936-943.

 

2011

  • Kohout M., Svoboda J., Novotná V., Pociecha D.: Non-symmetrical bent-shaped liquid crystals based on laterally substituted naphthalene central core with four ester groups. Liq. Cryst. 2011, 38, 1099-1110.
  • Kozmík V., Henke A., Řehová L., Kurfürst M., Slabochová M., Svoboda J., Novotná V., Glogarová M.: Liquid crystalline benzothiophene derivatives. Part 2. 2,5-Disubstituted benzothiophenes. Liq. Cryst. 2011, 38, 1245-1261.
  • Aaron J.-J., Párkányi C., Adenier A.,Potin C., Zajíčková Z., Martínez O. R., Svoboda J., Pihera P., Váchal P.: Fluorescence properties and dipole moments of novel fused thienobenzofurans. Solvent and structural effects. J. Fluorescence 2011, 21, 2133-2141.

 

2010

  • Kovářová A., Svoboda J., Novotná V., Glogarová M., Salamonczyk M., Pociecha D., Gorecka E.: [2]Benzothiophene bent-shaped liquid crystals. Liq. Cryst. 2010, 37, 1501-1513.
  • Kozmík V., Polášek P., Seidler A., Kohout M., Svoboda J., Novotná V., Glogarová M., Pociecha D.: The effect of a thiophene ring in the outer position on mesomorphic properties of the bent-shaped liquid crystals. J. Mater. Chem. 2010, 20, 7430-7435.
  • Kohout M., Svoboda J., Novotná V., Glogarová M., Pociecha D.: Non-symmetrical bent-shaped liquid crystals with five ester groups. Liq. Cryst. 2010, 37, 987-996.
  • Obadović D. Ž., Vajda A., Jákli A., Menyhárd A., Kohout M., Svoboda J., Stojanović M., Éber N., Galli G., Fodor-Csorba K.: Mesophase behaviour of binary mixtures of bell-shaped and calamitic compounds. Liq. Cryst. 2010, 37, 527-536.
  • Kohout M., Chambers M., Vajda A., Galli G., Domján A., Svoboda J., Bubnov A., Jákli A., Fodor-Csorba K.: Properties of non-symmetric bent-core liquid crystals with variable flexible chain length. Liq. Cryst. 2010, 37, 537-545.
  • Ledesma A. E., Contreras C., Svoboda J., Vektariane A., Brandán S. A.: Theoretical structures and experimental vibrational spectra of isomeric benzofused thieno[3,2-b]furan compounds. J. Mol. Struc. 2010, 967, 159-165.
  • Žurek J., Cibulka R., Dvořáková H., Svoboda J.: N1,N10-Ethylene-bridged flavinium salts derived from L-valinol: synthesis and catalytic activity in H2O2 oxidations. Tetrahedron Lett. 2010, 51, 1083-1086.
  • Weissflog W., Pelzl G., Kresse H., Baumeister U., Brand K., Schröder M. W., Tamba M. B., Findeisen-Tandel S., Kornek U., Stern S., Eremin A., Stannarius A. , Svoboda J.: In search of a new design strategy for solid single-component organic ferroelectrics: Polar crystalline phases formed by bent-core molecules. J. Mater. Chem. 2010, 20, 6057.
  • Lô C., Aaron J.-J., Kozmík V., Svoboda J., Brochon J.-C., Na L.: Synthesis, electrochemical, and optical properties of new fluorescent substituted thieno[3,2-b][1] benzothiophenes. J. Fluorescence 2010, 20(5), 1037-1047.
  • Glogarová M., Hampl F.,Lejček L., Novotná V., Svoboda J., Cigl M.: Experimental proof of symmetry breaking in tilted smectics composed of molecules with axial chirality. J. Chem. Phys. 2010, 133, 221102/1-221102/4.

 

2009

  • Kohout M., Svoboda J., Novotná V., Pociecha D., Glogarová M., Gorecka E.: Nematic-polar columnar phase sequence in new bent-shaped liquid crystals based on 7-hydroxynaphthalene-2-carboxylic acid core. J. Mater. Chem. 2009, 19, 3153-3160.
  • Machara J., Kozmík V., Pojarová M., Dvořáková H., Svoboda J.: Preparation and rearrangement study of novel thiophenium- and selenophenium-ylides. Collect. Czech. Chem. Commun. 2009, 74, 785-798.
  • Vektariene A., Vektaris G., Svoboda J.: A theoretical approach to the nucleophilic behavior of benzofused thieno[3.2-b]furans using DFT and HF based reactivity descriptors. Arkivoc 2009, 311-329.
  • Vaupotić N., Szydlowska J., Salamonczyk M., Kovářová A., Svoboda J., Osipov M., Pociecha D., Gorecka E.: Structure studies of the nematic phase formed by bent-core molecules. Phys. Rew. E. 2009, 80, 030701(R)
  • Salamonczyk M., Kovářová A., Svoboda J., Pociecha D., Gorecka E.: Switchable fluorescent liquid crystals. Appl. Phys. Lett. 2009, 95, 171901.

 

2008

  • Kurfürst M., Kozmík V., Svoboda J., Novotná V., Glogarová M.: Liquid crystalline benzothiophene derivatives. Liq. Cryst. 2008, 35, 21.
  • Sedlák M., Drabina P., Lánský V., Svoboda J.: Synthesis and characterization of substituted (benzo[b]thiophen-2-yl)-4-methyl-4,5-dihydro-1H-imidazol-5-ones. J. Heterocycl. Chem. 2008, 45, 859.
  • Lô C., Adenier A., Maurel F., Aaron J.-J., Kozmík V., Svoboda J..: Electrochemical, spectral and theoretical studies of two new methylthieno[3,2-b]benzothiophenes and their polymers electrosynthesized in organic and micellar media. Synth. Metals 2008, 158, 6-24.
  • Novotná V., Žurek J., Kozmík V., Svoboda J., Glogarová M.: Novel hockey-stick mesogens with the nematic, synclinic and anticlinic smectic C phase sequence. Liq. Cryst. 2008, 35, 1023.
  • Lô C., Aaron J.-J., Svoboda J., Brochon J. C., Na L.: Fluorescence study of new thienobenzothiophene substituted derivatives for luminiscent materials. Luminiscence 2008, 23, 240.
  • Obadović D.Z., Vajda A., Jákli A., Kohout M., Stojanović M., Éber N., Fodor-Csorba K., Galli G.: Phase Sequences of Mixtures Formed by Bell-shaped and Calamitic Compound. J. Res. Phys. 2008, 32, 69-74.

 

2007

  • Machara A., Pojarová M., Svoboda J.: Synthesis and cycloaddition reaction of 3-vinylthieno[3,2-b][1]benzothiophene. Collect. Czech. Chem. Commun. 2007, 72, 952-964.

 

2006

  • Kozmík V., Kovářová A., Kuchař M., Svoboda J., Novotná V., Glogarová M., Kroupa J.: Novel polymerizable bent-shaped monomeric molecules. Liq. Cryst., 2006, 33, 41.
  • Kozmík V., Košata B., Svoboda J., Kuchař M.: A study of 5-nitroindole alkylation Collect. Czech. Chem. Commun., 2006, 71, 679.
  • Lô C., Adenier A., Chane-Ching K., Maurel F., Aaron J. J., Košata B., Svoboda J..: A novel fluorescent, conducting polymer: Poly[1-(thiophene-2-yl)benzothieno[3,2-b]benzothiophene) electrosynthesis, characterization and optical properties. Synth. Metals 2006, 156, 256.
  • Černovská K., Košata B., Svoboda J., Novotná V., Glogarová M.: Novel ferroelectric liquid crystals based on fused thieno[3,2 b]furan and thieno[3,2 b]thiophene core. Liq. Cryst. 2006, 33, 987.
  • Aaron J.-J., Mézlová M., Capochichi M., Svoboda J., Brochon J.-C., Guiot E.: Fluorescence properties of new fused thienoindoles and their conductiong oligomers? Evidence for a heavy atom quenching effect. Luminiscence 2006, 21, 330.
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News

January 2024

Our contribution to the Science of Synthesis has been published:

T. Tobrman, 9.14.5 Phospholes (Update 2024),  Science of Synthesis, 2024, DOI: https://science-of-synthesis.thieme.com/app/text/?id=SD-109-00525&position=1

 

October 2023

Sergej Mrkobrada defended the diploma thesis.

 

June 2023

Denisa Skurková defended the bachelor's thesis.

One-day river trip from Týnec nad Sázavou to Pikovice.

 

February 2023

Zdeněk Hartman was admitted to the University of Cambridge. Congratulations!

 

December 2022

In collaboration with Prof. Cibulka’s group, we published the preparation of arylated flavins: 

Marek Čubiňák, Naisargi Varma, Petr Oeser, Adam Pokluda, Tetiana Pavlovska, Radek Cibulka,
 Marek Sikorski, and Tomáš Tobrman, Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C-C Bond Coupling. J. Org. Chem. 2022, DOI: 10.1021/acs.joc.2c02168.

 

Autumn 2022

Andrea Blahovcová, Hana Hovorková and Marek Filippi joined our group.

 

August 2022

Aleš Krčil defended the diploma thesis.

 

June 2022

Soňa Poláčková a Scarlet Stefanie Vraník defended the diploma thesis.

 

June2022

One-day river trip from Vyššího Brod to Český Krumlov.

June 2022

Karolína Šilhánová defended the bachelor's thesis.

October 2019

Veronika Budková a Nikola Studničková joined our group.

October 2019

We have published stereoselective synthesis of trisubstituted alkenes: J. Organomet. Chem., Stereoselective synthesis of trisubstituted alkenyl Fischer aminocarbenes through self-mediated α-haloketone olefination, https://doi.org/10.1016/j.jorganchem.2019.120971

September 2019

We have published a review on the use of indolylboronic acids in organic synthesis: Molecules, Indolylboronic Acids: Preparation and Applications. 2019, 24, 3523. https://www.mdpi.com/1420-3049/24/19/3523

July 2019

Tereza Edlová created a laboratory logo:

June 2019
Peter Polak won the J.-M. Lehn prize for chemistry 2020 and Marek Čubiňák finished third in the Synthon Award 2019!

January 2019:
Aleš Krčil, Jan Bejblík and Karolína Šilhánová joined our group.

 
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Current group members

Students:      

PhD students:      

Assoc. Prof.:

  • Zdeněk Hartman
    (Secondary School Student)

  • Magdaléna Holasová
    (Collaboration with Ivo Starý  Group - IOCB)

  • Aleš Krčil

  • Sergej Mrkobrada

  • Soňa Poláčková

  • Karolína Šilhánová

  • Scarlet Stefanie Vraník

 

 

Tomáš Tobrman

Department of Organic Chemistry

UCT Prague

Technická 5

166 28 Praha 6

tel: +420 220 444 245

fax: +420 220 444 288

tomas.tobrman@vscht.cz

Technician:

Marta Tokárová


Our alumni:

 

PhD students: Master students: Bachelor students:

Visiting students:

  • Peter Polák (2020)
  • Vladislav Kotek (2015)
  • Martin Křováček (2011)
  • Tomáš Tobrman (2005)
  • Luděk Meca (2004)
  • Martina Havelková (2002)
  • Miroslav Havránek (1998)
  • Tereza Edlová (2021)
  • Eva Ostapenko (2021)
  • Artem Petrenko (2020)
  • Jakub Koudelka (2020)
  • Petr Oeser (2020)
  • Václav Vraštil (2019)
  • Marek Čubiňák (2018)
  • Eliška Fikejzlová (2018)
  • Filip Gracias (2018)
  • Jiří Lapčík (2017)
  • Kristýna Kolouchová (2016)
  • Lukáš Lattenberk (2016)
  • Iegor Vyshnytskyi (2016)
  • Peter Polák (2015)
  • Hana Váňová (2015)
  • Petr Koukal (2013)
  • Ivana Jurásková (2012)
  • Ivana Nousková (2011)
  • Ivana Kubíčková (2011)
  • Petra Slavíková (2009)
  • Markéta Šmídková (2009)
  • Miroslava Tobrmanová (2007)
  • Martin Klečka (2007)
  • Jaroslav Padevět (2006)
  • Jana Roháčová (2005)
  • Jiří Černý (2002)
  • Dušan Drahoňovský (2000)
  • Ivan Rotrekl (2000)
  • Martin Studenovský (1999)
  • Petr Suchý (1996)
  • Roman Wágner (1995)
  • Veronika Budková (2021)
  • Jan Bejblík (2020)
  • Aleš Krčil (2020)
  • Karolína Šilhánová (2020)
  • Eva Ostapenko (2019)
  • Tereza Edlová (2019)
  • Matúš Drexler (2019)
  • Jakub Koudelka (2018)
  • Petr Oeser (2018)
  • Roman Valeš (2017)
  • Václav Vraštil (2017)
  • Marek Čubiňák (2016)
  • Eliška Fikejzová (2016)
  • Lukáš Lattenberk (2014)
  • Hana Váňová (2013)
  • Peter Polák (2013)
  • Michal Maryška (2012)
  • Šárka Pěchoučková (2011)
  • Gabriel Tóth (2008)
  • Baptiste Chartier (France, 2021)
  • Antoine Catinaud (France, 2019)
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The research activities of our group are focused on the application of the reactivity of transition metals in the following areas:

Design of new reactions and processes for the preparation of heterocyclic compounds

Research activities associated with the chemistry of heterocyclic compounds can be demonstrated by the synthesis of pentasubstituted phosphols by copper-catalyzed C-H activation of 1,3,4-trisubstituted phospholes:

Polák, P.; Tobrman, T. Formal Transition-Metal-Catalyzed Phosphole C–H Activation for the Synthesis of Pentasubstituted Phospholes.
Org. Lett. 2020, 22, 2187-2190. DOI: 10.1021/acs.orglett.0c00359

Another use of transition-metal-catalyzed reactions is represented by the preparation of trisubstituted pyrroles using a dearomatization strategy:

Polák, P.; Tobrman, T. Dearomatization Strategy for the Synthesis of Arylated 2H-Pyrroles and 2,3,5-Trisubstituted 1H-Pyrroles.
Org. Lett. 201719, 4608-4611. DOI: 10.1021/acs.orglett.7b02219



Cross-coupling reactions of activated C-O bonds for the preparation of tetrasubstituted alkenes

The use of activated C-O bonds is an attractive alternative to organohalogen-based electrophilic templates. From a number of ways to activate C-O bonds, we pay attention to reactivity of enol-phosphates. We have recently published a new methodology for the preparation of tamoxifen that uses enol phosphate as a starting compound:

Kotek, V.; Polák, P.; Dvořáková, H.; Tobrman, T. Aluminium Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues
Eur. J. Org. Chem. 2016, 5037-5044. DOI: 10.1002/ejoc.201600959

 Cross-coupling reactions of activated C-O bonds were also used for the preparation of 2,3-disubstituted-1,3-dienes, [3]- and [4]dendralenes:

Polák, P.; Tobrman, T. Novel Selective Approach to Terminally Substituted [n]Dendralenes.
Eur. J. Org. Chem. 2019, 957-968. DOI:10.1002/ejoc.201801522

 

We also described the synthesis of biologically active substance starting from enol phosphate:

Polák, P.; Tobrman, T. The synthesis of polysubstituted indoles from 3-bromo-2-indolyl phosphates
Org. Biomol. Chem. 201715, 6233-6241. DOI:10.1039/C7OB01127J

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2024

2023

  • J. Koudelka, M. Vosmanská and T. Tobrman, Synthesis of Sulfonic Acid Salts and Sulfonic Acids by Advanced Cross-Coupling Reaction of Vinyl Sulfonates. ChemistrySelect 2023, 8, e202304246. DOI:10.1002/slct.202304246

  • T. Tobrman, Vinyl Esters and Vinyl Sulfonates as Green Alternatives to Vinyl Bromide for the Synthesis of Monosubstituted Alkenes via Transition-Metal-Catalyzed Reactions. Chemistry 2023, 5, 2288–2321. DOI:10.3390/chemistry5040153

  • L. Koláčná, P. Polák, A. Liška, T. Tobrman and J. Ludvík, Pentasubstituted Phospholes with extended π-conjugated Arm – Synthesis, electrochemistry, spectra and quantum chemical calculations. Electrochim. Acta 2023, 468, 143073. DOI: 10.1016/j.electacta.2023.143073

  • M. Čubiňák, N. Varma, P. Oeser, A. Pokluda, T. Pavlovska, R. Cibulka, M. Sikorski, T. Tobrman, Tuning the Photophysical Properties of Flavins by Attaching an Aryl Moiety via Direct C–C Bond Coupling. J. Org. Chem. 2023, 88, 218–229. DOI: 10.1021/acs.joc.2c02168

2022

  • Tobrman, T.; Mrkobrada, S., Palladium-Catalyzed Cross-Coupling Reactions of Borylated Alkenes for the Stereoselective Synthesis of Tetrasubstituted Double Bond. Organics 2022, 3, 210.10.3390/org3030017

  • Shishkanova, T. V.; Tobrman, T.; Otta, J.; Broncová, G.; Fitl, P.; Vrňata, M., Substituted polythiophene-based sensor for detection of ammonia in gaseous and aqueous environment. J. Mater. Sci. 2022, 57, 1787017882. DOI: 10.1007/s10853-022-07694-8

  • Oeser, P.;  Petrenko, A.; Edlová, T.; Čubiňák, M.; Koudelka, J.; Tobrman, T., Halocyclobutanol Dehydration En Route to Halocyclobutenes. Synthesis 2022, 54, 3239–3248. DOI: 10.1055/a-1794-0685

  • Koláčná, L.; Klíma, J.; Polák, P.; Tobrman, T.; Liška, A.; Ludvík, J., Electrochemical, EPR, and computational study of pyrene conjugatesprecursors for novel type of organic semiconductors. J. Solid State Electrochem. 2022, 26, 503514. DOI: 10.1007/s10008-021-05094-7

2021

  • Oeser, P; Koudelka, J.; Petrenko, A.; T. Tobrman, Recent Progress Concerning the N-Arylation of Indoles. Molecules 2021, 26, 5079. DOI: 10.3390/molecules26165079  
  • Čubiňák, M.; Bigeon, J.; Galář, P.; Ondič, L.; Tobrman, T., The Synthesis of Tetrasubstituted Cycloalkenes Bearing π-Conjugated Substituents and Their Optical Properties. ChemistrySelect 2021, 6, 99049910. DOI: 10.1002/slct.202103122
  • Oeser, P.; Edlová, T.; Čubiňák, M.; Tobrman, T., Transition-Metal-Free Ring-Opening Reaction of 2-Halocyclobutanols through Ring Contraction. Eur. J. Org. Chem. 2021, 49584967. DOI: 10.1002/ejoc.202100837
  • Koudelka, J.; Tobrman, T., Synthesis of 2-Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence. Eur. J. Org. Chem. 2021, 3260–3269 DOI:10.1002/ejoc.202100464

  • Edlová, T.; Dvořáková, H.; Eigner, V.; Tobrman, T., Substrate-Controlled Regioselective Bromination of 1,2-Disubstituted Cyclobutenes: An Application in the Synthesis of 2,3-Disubstituted Cyclobutenones.
    J. Org. Chem. 2021, 86, 5820–5831 DOI:10.1021/acs.joc.1c00261

  • Shishkanova, T.; Stepánková, N.; Tlustý, M.; Tobrman, T.; Jurásek, B.; Kuchař, M.; Trchová, M.; Fitl, P.; Vrňata, M., Electrochemically oxidized 15-crown-5 substituted thiophene and host-guest interaction with new psychoactive substances Electrochim. Acta 2021, 737, 137862 DOI:10.1016/j.electacta.2021.137862

  • Edlová, T.; Čubiňák, M.; Tobrman, T., Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis. Synthesis 2021, 53, 255266. DOI: 10.1055/s-0040-1707270

2020

  • Oeser, P.; Koudelka, J.; Dvořáková, H.; Tobrman, T., Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents. RSC Adv. 2020, 10, 3510935120. DOI: 10.1039/D0RA07472A

  • Čubiňák, M.; Tobrman, T., Room-Temperature Negishi Reaction of Trisubstituted Vinyl Phosphates for the Synthesis of Tetrasubstituted Alkenes. J. Org. Chem. 2020, 85, 1072810739. DOI: 10.1021/acs.joc.0c01254

  • Polák, P.; Čejka, J.; Tobrman, T., Formal Transition-Metal-Catalyzed Phosphole C–H Activation for the Synthesis of Pentasubstituted Phospholes. Org. Lett. 2020, 22, 21872190. DOI: 10.1021/acs.orglett.0c00359

  • Tobrman, T; Krupička, M.; Polák, P.; Dvořáková, H.; Čubiňák, M.; Babor, M.; Dvořák, D., Diastereoselective Cyclopropanation through Michael Addition‐Initiated Ring Closure between α,α‐Dibromoketones and α,β‐Unsaturated Fischer Carbene Complexes. Eur. J. Org. Chem. 2020, 429436. DOI: 10.1002/ejoc.201901503

  • Guricová, M.; Tobrman, T; Pižl, M.; Žižková, S.; Hoskovcová, I.; Dvořák, D., Synthesis, characterisation and electrochemical properties of Cr(0) aminocarbene complexes containing condensed heteroaromatic moiety. J. Organomet. Chem. 2020, 905, 121023 DOI: 10.1016/j.jorganchem.2019.121023

2019

  • Tobrman, T.; Čubiňák, M.; Dvořák, D., Stereoselective synthesis of trisubstituted alkenyl Fischer aminocarbenes through self-mediated α-haloketone olefination. J. Organomet. Chem. 2019, 902, 120971. DOI: 10.1016/j.jorganchem.2019.120971

  • Čubiňák, M.; Edlová, T.; Polák, P.; Tobrman, T., Indolylboronic Acids: Preparation and Applications.
    Molecules 2019, 24, 3523 DOI: 10.3390/molecules24193523

  • Váňová, H.; Tobrman, T.; Babor, M.; Dvořák, D., Reaction of lithiated thiophene-derived aminocarbene complexes with inorganic halides: Preparation of a heteroatom containing mono- and multicarbene complexes. J. Organomet. Chem. 2019, 882, 9095 DOI: 10.1016/j.jorganchem.2018.12.015

  • Tobrman, T.; Polák, P.; Čubiňák, M.; Dvořáková, H.; Dvořák, D., Dichotomy within 1,4-addition of organolithium and Grignard reagents to α,β-unsaturated Fischer alkoxycarbenes: A new synthesis of Fischer carbenes. Tetrahedron 2019, 75, 21752181 DOI: 10.1016/j.tet.2019.02.038

  • Polák, P.; Tobrman, T., Novel Selective Approach to Terminally Substituted [n]Dendralenes
    Eur. J. Org. Chem. 2019, 957968. DOI:10.1002/ejoc.201801522

2018

  • Čubiňák, M.; Eigner, V.; Tobrman, T., Bench-Stable Sulfoxide-Based Boronates: Preparation and Application in a Tandem Suzuki Reaction. Adv. Synth. Catal. 2018, 360, 46044614 DOI: 10.1002/adsc.201801000

2017

  • Polak, P.; Dvorak, D.; Tobrman, T., Cyanogen: A Versatile Reagent for Diversity-​Oriented Synthesis
    Synthesis 2017, 49, 17571766 DOI:10.1055/s-0036-1588410

  • Polak, P.; Tobrman, T., The synthesis of polysubstituted indoles from 3-​bromo-​2-​indolyl phosphates. Org. Biomol. Chem. 2017, 15, 62336241 DOI:10.1039/C7OB01127J

  • Polak, P.; Tobrman, T., Dearomatization Strategy for the Synthesis of Arylated 2H-​Pyrroles and 2,​3,​5-​Trisubstituted 1H-​Pyrroles. Org. Lett. 2017, 19, 4604611 DOI: 10.1021/acs.orglett.7b02219

  • Šimůnková, N.; Tobrman, T.; Eigner, V.; Dvořák, D., A Study on the Intramolecular Mitsunobu Reaction of N6-(ω-hydroxyalkyl)adenines. J. Heterocyclic Chem 2017, asap DOI: 10.1002/jhet.2982

2016

  • Váňová, H.; Tobrman, T.; Hoskovcova, I.; Dvořák, D., Modular synthesis of Fischer biscarbene complexes of chromium. Organometallics 2016, 35, 29993006. DOI:10.1021/acs.organomet.6b00527

  • Kotek, V.; Polák, P.; Dvořáková, H.; Tobrman, T., Aluminium Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues. Eur. J. Org. Chem. 2016, 50375044. DOI:10.1002/ejoc.201600959

  • Polák, P.; Váňová, H.; Dvořák, D.; Tobrman, T., Recent Progress in Transition Metal-Catalyzed Stereoselective Synthesis of Acyclic All-Carbon Tetrasubstituted Alkenes. Tetrahedron Lett. 2016, 57, 36843693. DOI:10.1016/j.tetlet.2016.07.030 

  • Kotek, V.; Polák, P.; Tobrman, T., Efficient and Simple Preparation of Functionalized 1,1-Dibromoenol Phosphates. Monat. Chem. 2016, 147, 405412. DOI:10.1007/s00706-015-1613-6


2015

  • Kotek V., Dvořáková H., Tobrman T., Modular and highly stereoselective approach to all-carbon tetrasubstituted alkenes. Org. Lett., 2015, 17, 608611. DOI: 10.1021/ol503624v
  • Křováček M., Dvořák D.: Synthesis of potentially biologically active 6-(1,3-butadiynyl)purines. J. Heterocyclic Chem., 2015, 52, 4047. DOI: 10.1002/jhet.1938

 

2014

  • Tobrman T., Jurásková I., Dvořák D., Negishi cross-coupling reaction as a simple and efficient route to functionalized amino and alkoxy carbene complexes of chromium, molybdenum, and tungsten. Organometallics, 2014, 33, 65936603. DOI: 10.1021/om500925m
  • Kvapilová H., Eigner V., Hoskovcová I., Tobrman T., Čejka J., Záliš S., Structural flexibility of 2-hetaryl chromium aminocarbene complexes: Experimental and theoretical evidence. Inorg. Chim. Acta, 2014, 421, 439445. DOI: 10.1016/j.ica.2014.06.028
  • Vrzal L., Flídrová K., Tobrman T, Dvořáková H., Lhoták, P., Use of residual dipolar couplings in conformational analysis of meta-disubstituted calix[4]arenes. Chem. Commun., 2014, 50, 75907592. DOI: 10.1039/C4CC02274B
  • Tobrman T, Jurásková I., Váňová H., Dvořák D, Lithiation of chromium and tungsten aminocarbene complexes: An easy approach to functionalized aminocarbene complexes. Organometallics, 2014, 33, 29902996. DOI: 10.1021/om500182p
  • Tobrman T., Dvořák D., Regioselective and facile synthesis of 7,9-dialkyl-8-oxopurines from 7,9-dialkyl-7,8-dihydropurines: Total synthesis of Heteromines I and J. Synthesis, 2014, 46, 660668. DOI: 10.1055/s-0033-1340499

 

2013

  • Maryška M., Chudíková N., Kotek V., Dvořák D., Tobrman T., Regioselective and efficient synthesis of N7-substituted adenines, guanines, and 6-mercaptopurines. Monatsh. Chem. 2013, 144, 501507. DOI: 10.1007/s00706-012-0899-x
  • Koukal P., Dvořáková H., Dvořák D., Tobrman T., Palladium-Catalyzed Claisen Rearrangement of Allyloxypurines. Chem. Pap., 2013, 67, 38. DOI: 10.2478/s11696-012-0239-y

 

2012

  • Metelková R., Tobrman T., Kvapilová H., Hoskovcová I., Ludvík J., Synthesis, characterization and electrochemical investigation of hetaryl chromium(0) aminocarbene complexes. Electrochim. Acta, 2012, 82, 470477. DOI: 10.1016/j.electacta.2012.05.027
  • Kotek V., Tobrman T., Dvořák D., Highly Efficient and Broad-Scope Protocol for the Preparation of 7-Substituted 6-halopurines via N9-Boc-Protected 7,8-dihydropurines. Synthesis 2012, 44, 610618. DOI: 10.1055/s-0031-1290068

 

2011

  • Hoskovcová I., Zvěřinová R., Roháčová J., Dvořák D., Tobrman T., Záliš S., Ludvík J, Fischer aminocarbene complexes of chromium and iron: Anomalous electrochemical reduction of p-carbonyl substituted derivatives. Electrochim. Acta 2011, 56, 68536859. DOI: 10.1016/j.electacta.2011.05.096
  • Tobrmanová M., Tobrman T., Dvořák D., Pd-Catalyzed Allylic Substitution of Purin-8-yl(allyl) Acetate: Route to (E)-Alkenylpurines. Collect. Czech. Chem. Commun. 2011, 76, 311326. DOI: 10.1135/cccc2011030

 

2010

  • Negishi E.-i., Tobrman T., Rao H., Xu S., Lee Ch.-T., Highly (98 %) Selective Alkene Synthesis of Wide Applicability via Fluride-Promoted Pd-Catalyzed Cross-Coupling of Alkenylboranes. Isr. J. Chem. 2010, 50, 696701. DOI: 10.1002/ijch.201000051
  • Kotek V., Chudíková N., Tobrman T., Dvořák D., Selective Synthesis of 7-substituted Purines via 7,8-dihydropurines. Org. Lett. 2010, 12, 57245727. DOI: 10.1021/ol1025525
  • Pařík P., Kulhánek J., Ludwig M., Wagner R., Rotrekl I., Drahoňovský D., Meca L., Šmídková M., Tobrman T., Dvořák D., Acidity of Benzoic Acids Bearing the (CO)5Cr=CN(CH3)2 Group. Organometallics 2010, 29, 41354138. DOI: 10.1021/om100608x
  • Hoskovcová I., Roháčová J., Dvořák D., Tobrman T., Záliš S., Zvěřinová R., Ludvík J., Synthesis and electrochemical study of iron, chromium and tungsten aminocarbenes: Role of ligand structure and central metal nature. Electrochim. Acta, 2010, 55, 83418351. DOI: 10.1016/j.electacta.2010.02.057
  • Klečka M., Křováček M., Tobrman T., Dvořák D., Synthesis of (E)-6-Alkenylpurines via Pd-Catalyzed Stannation/Protodestannation Tandem Process of Alkynylpurines. Collect. Czech. Chem. Commun. 2010, 75, 313332. DOI: 10.1135/cccc2009563
  • Wang C., Xu Z., Tobrman T., Negishi E.-i., Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of >98% Isomeric Purity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes. Adv. Synth Catal., 2010, 352, 627631. DOI: 10.1002/adsc.200900766

  

2009-1996

  • Wang C., Tobrman T., Xu Z., Negishi E.-i., Highly Regio- and Stereoselective Synthesis of (Z)-Trisubstituted Alkenes via Propyne Bromoboration and Tandem Pd-Catalyzed Cross-Coupling. Org. Lett. 2009, 11, 40924095. DOI: 10.1021/ol901566e
  • Keder R., Dvořáková H., Dvořák D., New Approach to the Synthesis of N-7-Arylguanines and N-7-Aryladenines. Eur. J. Org. Chem. 2009, 15221531. DOI: 10.1002/ejoc.200801002
  • Tobrman T., Dvořák D., Heck reactions of 6- and 2-halopurines. Eur. J. Org. Chem. 2008, 2923–2928. DOI: 10.1002/ejoc.200800091
  • Krouželka J., Linhart I., Tobrman T., Synthesis of 3-(2-hydroxy-1-phenylethyl)- and 3-(2-hydroxy-2-phenylehtyl)adenine, DNA adducts derived from styrene. J. Heterocyclic Chem. 2008, 45, 789–795. DOI: 10.1002/chin.200838155
  • Tobrman T., Štepnička P., Císařová I., Dvořák D., Preparation and crystal structures of purine 2,2’-, 6,6’-, and 8,8’-dimers. Eur. J. Org. Chem. 2008, 2167–2174. DOI: 10.1002/ejoc.200800017
  • Tobrman T., Dvořák D., Reductive Dimerization of 2- and 6-Iodopurines: Side reaction in Pd-Catalyzed Cross Coupling of Iodopurines. Collect. Czech Chem. Comm. 2007, 72, 13651374. DOI: 10.1135/cccc20071365
  • Tobrman T., Dvořák D., Selective magnesiation of chloro-iodopurines: An efficient approach to new purine derivatives. Org. Lett. 2006, 8, 12911294. DOI: 10.1021/ol053013w
  • Tobrman T., Meca L., Dvořáková H., Černý J., Dvořák D., Study of the Origin of the Hindered Rotation of an Aryl Ring in the Chromium Aminocarbene Complexes Bearing Aromatic Ring Atteched to the Carbene Carbon Atom. Organometalics 2006, 25, 55405548. DOI: 10.1021/om0605837
  • Klečka M., Tobrman T., Dvořák D., Cu(I)-catalyzed coupling of (9-benzylpurin-6-yl)magnesium chloride with allyl halides: an approach to 6-allylpurine derivatives. Collect. Czech Chem. Comm. 2006, 71, 12211228. DOI: 10.1135/cccc20061221
  • Hoskovcová I., Roháčová J., Meca L., et al., Electrochemistry of chromium(0)-aminocarbene complexes: The use of intramolecular interaction LFER for characterization of the oxidation and reduction centre of the complex. Electrochim. Acta 2005, 50, 49114915. DOI: 10.1016/j.electacta.2004.12.047
  • Drahoňovský D., Štěpnička P., Dvořák D., P-chiral 2-{1 '-[butyl(phenyl)phosphanyl]ferrocen-1-yl} -4-isopropyl-4,5-dihydrooxazoles: A second chirality center in catalytic system. Collect. Czech Chem. Comm. 2005, 70, 361369. DOI: 10.1135/cccc20050361
  • Meca L., Dvořák D., Ludvík J., et al., Synthesis, structures, and electrochemistry of group 6 aminocarbenes with a P-chelating 1'-(Diphenylphosphino)ferrocenyl substituent Organometallics 2004, 23, 25412551. DOI: 10.1021/om040007f
  • Tobrman T., Dvořák D., 'Reductive Heck reaction' of 6-halopurines. Tetrahedron Lett. 2004, 45, 273276. DOI: 10.1016/j.tetlet.2003.10.181
  • Tobrman T., Dvořák D., 6-Magnesiated purines: Preparation and reaction with aldehydes. Org. Lett. 2003, 5, 42894291. DOI: 10.1021/ol0355027
  • Hocek M., Dvořák D., Havelková M., Covalent analogues of nucleobase-pairs. Nucleoside Nucleotides & Nucleic Acids 2003, 22, 775777. DOI: 10.1081/NCN-120022632
  • Meca L., Císařová I., Dvořák D., Thermolysis of iron N-allylaminocarbene complexes: Formation of eta(3)-1-azaallylirontricarbonyl complexes. Synthetic and theoretical study. Organometallics 2003, 22, 37033709. DOI: 10.1021/om0301280
  • Drahoňovský D., Borgo V., Dvořák D., Fischer chromium carbene complexes as nucleophiles in palladium-catalyzed allylic substitution reactions. Tetrahedron Lett. 2002, 43, 78677869. DOI: 10.1016/S0040-4039(02)01913-5
  • Havelková M., Dvořák D., Hocek M., Covalent analogues of DNA base-pairs and triplets. Part 3: Synthesis of 1 ,4-and 1,3-bis(purin-6-yl)benzenes and 1-(1,3-dimethyluracil-5-yl)-3 or 4-(purin-9-yl)benzenes. Tetrahedron 2002, 58, 74317435. DOI: 10.1016/S0040-4020(02)00833-5
  • Havránek M., Dvořák D., 3,3-disubstituted allyl alcohols from palladium-catalyzed coupling of hydroaluminated propargyl alcohols with aryl iodides. J. Org. Chem. 2002, 67, 21252130. DOI: 10.1021/jo0162235
  • Vyklický L., Dvořáková H., Dvořák D., Iron aminocarbene complexes containing a double C=C bond in the N-substituent: Preparation and reactivity. Organometallics 2001, 20, 54195424. DOI: 10.1021/om010533w
  • Havelková M., Dvořák D., Hocek M., The Suzuki-Miyaura cross-coupling reactions of 2-, 6-or 8-halopurines with boronic acids leading to 2-, 6-or 8-aryl- and -alkenylpurine derivatives. Synthesis 2001, 17041710. DOI: 10.1055/s-1999-2753
  • Drahoňovský D., Císařová I., Štěpnička P., et al., An alternative approach to chiral 2-[1 '-(diphenylphosphanyl)ferrocenyl]-4,5-dihydrooxazoles. Collect. Czech. Chem. Commun. 2001, 66, 588604. DOI: 10.1135/cccc20010588
  • Rotrekl I., Vyklický L., Dvořák D., Reaction of iron aminocarbene complexes with electronically deficient alkenes. J. Organometallic Chem. 2001, 617, 329333. DOI: 10.1016/S0022-328X(00)00707-5
  • Havelková M., Studenovský M., Dvořák D., N-1-substituted hypoxanthine derivatives from the reaction of 6-halopurines with Michael acceptors under the conditions of Heck reaction. Collect. Czech. Chem. Commun. 2000, 65, 797804. DOI: 10.1135/cccc20000797
  • Havránek M., Dvořák D., 3-(tributylstannyl)allyl alcohols: Useful building blocks for solid-phase synthesis of skipped dienes and trienes. Collect. Czech. Chem. Commun. 2000, 65, 434454. DOI: 10.1135/cccc20000434
  • Havelková M., Hocek M., Česnek M., et al., The Suzuki-Miyaura cross-coupling reactions of 6-halopurines with boronic acids leading to 6-aryl- and 6-alkenylpurines. Synlett 1999, 11451147. DOI: 10.1055/s-1999-2753
  • Suchý P., Dvořák D., Havelková M., Unexpected course of the reaction of 1,3-bis(dimethylamino)trimethinium perchlorate with 3-substituted prop-2-ynals leading to 1-aryl-2,4,6-triformylbenzenes. Collect. Czech. Chem. Commun. 1999, 64, 119129. DOI: 10.1135/cccc19990119
  • Dvořáková H., Dvořák D., Holý A., Synthesis of acyclic nucleotide analogues derived from 6-(sec- or tert-alkyl)purines via coupling of 6-chloropurine derivatives with organocuprates. Collect. Czech. Chem. Commun. 1998, 63, 20652074. DOI: 10.1135/cccc19982065
  • Havránek M., Dvořák D., Transmetallation from aluminum to tin: A facile preparation of tributylstannylprop-2-en-1-ols. Synthesis 1998, 12641268. DOI: 10.1055/s-1998-6101
  • Dvořák D., Ludwig M., [(N,N-dimethylamino)carboxymethylene]pentacarbonyl-chromium(0): The first Fischer carbene complex with a free carboxyl group attached directly to the carbene atom. Organometallics 1998, 17, 36273629. DOI: 10.1021/om980082o
  • Dvořák D., Transition metals in organic synthesis - Basic principles. Chemické Listy 1997, 91, 216226.
  • Arnold Z., Dvořák D., Havránek M., Convenient preparation of 1,3-bis(dimethylamino)trimethinium perchlorate, tetrafluoroborate and hexafluorophosphate. Collect. Czech. Chem. Commun. 1996, 61, 16371641. DOI: 10.1135/cccc19961637
  • Wagner R., Dvořák D., Holý A.: New application of the Stille coupling in the synthesis of 5-substituted uracils. Collect. Czech. Chem. Commun. 1996, 61, S118S119 Sp. Iss. SI. DOI: 10.1135/cccc1996s118
  • Dvořáková H., Dvořák D., Holý A., Coupling of 6-chloropurines with organocuprates derived from Grignard reagents: A convenient route to sec and tert 6-alkylpurines. Tetrahedron Lett. 1996, 37, 12851288. DOI: 10.1016/0040-4039(95)02375-5
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